letter orproof of beneficial ownership, such as your most recent account statement from that brokerage firm,as of the Record Date, a copy of the voting instruction form provided by your broker, bank, trustee, or nominee, or other similar evidence of record that confirms that you are

the beneficial owner of those sharesownership in order to attend the Annual Meeting online or vote electronically on any of the proposals in person at the Annual Meeting.

Sincerely,

Inga A. Fyodorova

Corporate Secretary

May 22, 2020April 29, 2021

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ONJUNE10, 2020. 9, 2021. The proxy statement and our Annual Report on Form10-K for fiscal year 20192020 (the “2019“2020 Annual Report”) are available at the website appearing on your proxy card. The notice of internet availability of proxy materials, the proxy statement, proxy card, and the 20192020 Annual Report will be providedmailed and/or made available to shareholders beginning on or about May 22, 2020.April 29, 2021.

CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS

This proxy statement includes “forward-looking statements” within the meaning of the “safe harbor” provisions of the Private Securities Litigation Reform Act of 1995. The expectations, estimates, and projections of the Company may differ from its actual results and consequently, you should not rely on these forward-looking statements as predictions of future events. Words such as “will,” “may,” “could,” “should,” “would,” “believe,” “expect,” “estimate,” “project,” “budget,“anticipate,” “forecast,” “anticipate,“future,” “intend,” “plan,” “may,” “will,” “could,” “should,” “believes,” “predicts,” “potential,” “continue,”“estimate” or the negative or other variations

Sodali LLCWe will also request brokerage houses,reimburse brokers, banks and other nominees, fiduciaries and custodians nomineeswho nominally hold shares of our common shares as of the Record Date for the reasonable costs they incur furnishing proxy solicitation and fiduciaries to forward proxyother required Annual Meeting materials to their customers or principalsstreet-name holders who arebeneficially own those shares on the beneficial owners of our Common Shares, and we will reimburse those persons for their expenses in doing so. We do not anticipate that the costs and expenses incurred in connection with this proxy solicitation will exceed those normally expended for a proxy solicitation for those matters to be voted on at the Annual Meeting.Record Date.

Proposals To Be Voted On

The business items to be voted on at the Annual Meeting are:

Proposal 1.The election of each of Steven J. Heyer, Andrew R. Heyer,Marc Magliacano, Jeffrey E. Stiefler and Leonard FluxmanWalter F. McLallen to serve as Class AB directors and to hold office for a three-year term expiring at the 20232024 annual meeting of shareholders;

Proposal 2.The ratification of the appointment of Ernst & Young LLP (“Ernst & Young”) to serve as our independent registered public accounting firm for the year ending December 31, 2020;

Proposal 3.The approval of the Private Placement (as defined below) for purposes of Nasdaq Listing Rule 5635; and

Proposal 4.The approval of the adoption of our Third Amended & Restated Memorandum of Association and Second Amended & Restated Articles of Association (the “Amended Articles”) to, among other things, authorize a new class ofnon-voting common shares, par value $0.0001 per share (the“Non-Voting Common Shares”).

Approval of Proposal 4 is conditioned upon approval of Proposal 3. Unless approval is received with respect to Proposal 3, we will not take any of the actions contemplated under Proposal 4. Shareholder approval of both Proposals 3 and 4 is required to consummate the Private Placement, unless the closing condition in the Investment Agreement related to shareholder approval of the Amended Articles is waived.2021;

We are not aware of any other matters that will be brought before the shareholders for a vote at the Annual Meeting. If any other matters are properly presented for a vote, then the individuals named as proxies will have discretionary authority, to the extent permitted by law, to vote on such matters according to their best judgment.

Proposal 1.You may vote “FOR” or “WITHHOLD” in the election of any or all nominees for election as a Class AB director. If you vote “withhold” authority to vote with respect to one or more director nominees, your vote will have no effect on the election of such nominees. Additionally, because the election of directors is not a “routine” or “discretionary” proposal under the applicable exchange rules, banks, brokers and other custodians will not have the authority to submit proxy cards on behalf of any beneficial owner from which it does not have instructions. Brokernon-votes will have no effect on the election of the nominees.

Proposal 2.You may vote “FOR,” “AGAINST” or “ABSTAIN” on the ratification of the appointment of our registered independent public accounting firm. Abstentions will have the effect of a vote against this proposal. Brokernon-votes will have no effect on the vote for this proposal.

Proposal 3.You may vote “FOR,” “AGAINST” or “ABSTAIN” on the proposal to approve the Private Placement pursuant to Nasdaq Listing Rule 5635. Abstentions will not be counted as votes “FOR” or “AGAINST” this proposal and will have no effect on the outcome of this proposal. Additionally, because this proposal is not a “routine” or “discretionary” proposal under the applicable exchange rules, banks, brokers and

other custodians will not have the authority to submit proxy cards on behalf of any beneficial owner from which it does not have instructions. Brokernon-votes will have no effect on the outcome of this proposal.

Proposal 4. You may vote “FOR,” “AGAINST” or “ABSTAIN” on the proposal to approve the adoption of our Amended Articles to, among other things, authorize a new class ofNon-Voting Common Shares. Abstentions will not be counted as votes “FOR” or “AGAINST” this proposal and will have no effect on the outcome of this proposal. Additionally, because this proposal is not a “routine” or “discretionary” proposal under the applicable exchange rules, banks, brokers and other custodians will not have the authority to submit proxy cards on behalf of any beneficial owner from which it does not have instructions. Brokernon-votes will have no effect on the outcome of this proposal.

Our Board of Directors recommends that you vote your shares:

In the election of Class AB directors, the affirmative vote of a plurality of the votes present in person or represented by proxy and entitled to vote on the election of directors is required. This means the director nominees receiving the greatest number of votes will be elected and withhold votes and brokernon-votes will have no effect on the outcome of the vote.

For the ratification of the appointment of the independent registered public accounting firm, the affirmative vote of a majority of the votes present in person or represented by proxy at the meeting and entitled to vote on such matter is required. Abstentions will have the effect of a vote against this proposal. Brokernon-votes will have no effect on the outcome of this proposal.

For the approval of the Private Placement for purposes of Nasdaq Listing Rule 5635, the affirmative vote of a majority of the votes cast on such matter is required. Abstentions and brokernon-votes will have no effect on the outcome of this proposal.

For the approval of the adoption of our Amended Articles to, among other things, authorize a new class ofNon-Voting Common Shares, the affirmative vote of a majority of the votes cast on such matter is required. Abstentions and brokernon-votes will have no effect on the outcome of this proposal.

On April 30, 2020, the Company entered into an Investment Agreement (the “Investment Agreement”) with Steiner Leisure Limited (“Steiner Leisure”), a current shareholder of the Company, and certain other investors, including members of the Company’s management and the Board of Directors (collectively, the“Co-Investors” and, together with Steiner Leisure, the “Investors”). The Investment Agreement provides for, among other things, the issuance and sale to the Investors of the Common Shares (as defined below) and warrants to purchase the Common Shares in exchange for an aggregate purchase price of $75.0 million (the “Private Placement”). Closing of the Private Placement is contingent upon, among other things, approval by the Company’s shareholders of Proposals 3 and 4.

Prior to the closing of the Private Placement, and assuming shareholder approval of Proposals 3 and 4, the Company will authorize a new class ofNon-Voting Common Shares, by adopting the Amended Articles. At closing, pursuant to the Investment Agreement, the Company will, among other things, (i) issue to Steiner Leisure an aggregate of (x) approximately 17.2 millionNon-Voting Common Shares and approximately 2.8 million of the Company’s voting common shares, par value $0.0001 per share (the “Voting Common Shares”, and together with the Non-Voting Common Shares, the “Common Shares”) (each amount includes the applicable portion of the Additional Shares (as defined below)), and (y) warrants to purchase approximately4.0 million Non-Voting Common Shares at an exercise price of $5.75 per share, and (ii) issue tothe Co-Investors an aggregate of (x) approximately 3.7 million of the Voting Common Shares and (y) warrants to purchase approximately 1.0 million Voting Common Shares at an exercise price of $5.75 per share, for an aggregate purchase price of $75.0 million. The Non-Voting Common Shares will be of equal rank to the Voting Common Shares in terms of dividends, liquidation, preferences and all other rights and features, with the following exceptions: (1) the Non-Voting Common Shares have no voting rights, except as may be required by law; (2) Steiner Leisure may vote its Non-Voting Common Shares in favor of its director designees; and (3) the Non-Voting Common Shares will automatically be converted to Voting Common Shares upon the occurrence of certain events.

Use of Proceeds

The Company intends to use the proceeds from the Private Placement for working capital or other general corporate purposes, and to (i) pay any costs, fees and expenses of the Company and (ii) pay or reimburse Steiner Leisure and its affiliates’ costs, fees and expenses (subject to a cap of $1.25 million), in each case, incurred in connection with the Private Placement.

Reasons for Shareholder Approval

Proposal 3. We are seeking shareholder approval of the Private Placement in order to comply with Nasdaq Listing Rule 5635, and because such shareholder approval is a condition to the closing of the Private Placement.

Under Nasdaq Listing Rule 5635(b), shareholder approval is required prior to the issuance of securities when the issuance or potential issuance will result in a “change of control” of the Company. This rule does not specifically define when a change in control may be deemed to occur, however, Nasdaq suggests in its guidance that a change of control would occur, subject to certain limited exceptions, if after a transaction a person or entity will hold 20% or more of a company’s then-outstanding capital stock and be that company’s largest shareholder. Based on this standard, the closing of the Private Placement would result in a change of control under Nasdaq Listing Rule 5635(b). Steiner Leisure and its affiliates currently beneficially own approximately 16.39% of our Common Shares (or approximately 14.0%, excluding the 1,486,520 Common Shares issuable upon exercise of warrants currently held by Steiner Leisure and its affiliates). If the Private Placement is consummated, Steiner Leisure will beneficially own more than 20% of our Common Shares, which will be the largest ownership position. Accordingly, we are seeking shareholder approval for this “change in control” as used in Nasdaq Listing Rule 5635(b). Shareholders should note that a “change of control” as described under Nasdaq Listing Rule 5635(b) applies only with respect to the application of such rule, and does not constitute a “change of control” for purposes of Bahamian law, our Articles, or any other purpose.

Under Nasdaq Listing Rule 5635(d), shareholder approval is required for a transaction (other than a public offering) involving the sale, issuance or potential issuance by an issuer of common shares (or securities convertible into or exercisable for common shares) at a price that is less than the “Minimum Price,” which is the lower of (i) the Nasdaq Official Closing Price (as reflected on Nasdaq.com) immediately preceding the signing of the binding agreement with respect to the issuance or (ii) the average Nasdaq Official Closing Price of the common shares (as reflected on Nasdaq.com) for the five trading days immediately preceding the signing of the binding agreement, with respect to the issuance if the number of common shares to be issued is or may be equal to 20% or more of the common shares, or 20% or more of the company’s voting power, outstanding immediately prior to the issuance. The securities being sold in the Private Placement are priced below the Minimum Price, and the Private Placement will result in the issuance of more than 20% of the Company’s voting power. Furthermore, pursuant to the Investment Agreement, none of the securities being sold in the Private Placement may be issued unless and until shareholder approval is received.

We are therefore seeking shareholder approval for the Private Placement in order to satisfy (i) the requirements of Nasdaq Listing Rule 5635, and (ii) our obligations under the Investment Agreement.

Proposal 4. We are seeking shareholder approval of Proposal 4 because it is a condition to the closing of the Private Placement.

Approval of Proposal 4 is conditioned upon approval of Proposal 3. Unless approval is received with respect to Proposal 3, we will not take any of the actions contemplated under Proposal 4. Shareholder approval of both Proposals 3 and 4 is required to consummate the Private Placement, unless the closing condition in the Investment Agreement related to shareholder approval of the Amended Articles is waived. Please see “Background to Proposals 3 and 4” for additional information regarding the reasons for Proposals 3 and 4. For a complete description of the terms of the Private Placement, see the section entitled “Proposal 3: Approval of the Private Placement for purposes of Nasdaq Listing Rule 5635”. For a description of the Amended Articles, see the section entitled “Proposal 4:Approval of the adoption of our Third Amended & Restated Memorandum of Association and Second Amended & Restated Articles of Association to authorize, among other things, a new class of Non-Voting Common Shares, par value $0.0001 per share”. The proposed form of the Amended Articles is included asAppendix B to this proxy statement. Shareholders should also carefully read the “Cautionary Note Regarding Forward-Looking Statements” section at the beginning of this proxy statement.

Yes, we engaged Nomura Securities International, Inc. (“Nomura”) as our financial advisor and placement agent with respect to the Private Placement. In addition, we engaged Duff & Phelps LLC (“Duff & Phelps”) to advise the Special Committee of the Board of Directors (the “Special Committee”), which committee was charged with evaluating different potential strategic alternatives for the Company, regarding, and to render to the Special Committee an opinion as to, the fairness, from a financial point of view, to the Company of the Private Placement. For more information, see the section entitled“Background to Proposals 3 and 4—Background of the Private Placement.” Duff & Phelps and Nomura were selected as financial advisors given, among other things, their respective qualifications, experience and reputation, and knowledge of and familiarity with the Company’s business and industry. Nomura was involved with the Company’s prior sale process and its business combination transaction and, based on that experience, was familiar with investors that had expressed interest in the Company in the past, and in a position to conduct potential investor outreach efforts in a targeted and expeditious manner. The Special Committee noted that Nomura previously served as a financial advisor to Steiner Leisure in connection with its sale of the Company and has provided services to Steiner Leisure and/or certain of its affiliates in connection with other matters, and engaged Duff & Phelps to provide an opinion regarding the fairness of any strategic transaction that it identified as desirable to present to the Board of Directors for consideration. On April 29, 2020, Duff & Phelps delivered its written opinion to the Special Committee that as of April 29, 2020, and based on and subject to the matters set forth in the opinion, the Private Placement was fair to the Company from a financial point of view. The full text of Duff & Phelps’s written opinion is included asAppendix Ahereto, and a summary of the written opinion is included under the section entitled “Background to Proposals 3 and 4—Opinion of Financial Advisor to the Special Committee.” Duff & Phelps’s opinion does not constitute a recommendation to any shareholder with respect to Proposals 3 or 4 or any of the other proposals to be considered at the Annual Meeting. We encourage you to read the opinion carefully in its entirety for a description of the assumptions made, matters considered and limitations on the review undertaken by Duff & Phelps.

We expect to announce preliminary voting results at the Annual Meeting and to publish final results in a Current Report on Form8-K that we will file with the Securities and Exchange Commission (the “SEC”)SEC within four business days following the meeting. The report will be available on our website at www.onespaworld.com and on the SEC’s website at www.sec.gov.www.sec.gov.

How You Can Vote

You are entitled to one vote for each of our voting common shares that you owned at the close of business on the Record Date. You may vote all shares owned by you on the Record Date, including (1) shares held directly in your name as the shareholder of record and (2) shares held for you as the beneficial owner through a bank, broker or other nominee.

Holders of non-voting common shares as of the Record Date are not entitled to vote at the Annual Meeting, except Steiner Leisure shall be entitled to one vote for each of its non-voting common shares that they owned on the Record Date in favor of the director nominee Marc Magliacano, the designated director of Steiner Leisure.

Beneficial Owner

If your shares are held through a bank, broker or other nominee, it is likely that they are registered in the name of the nominee and you are the beneficial owner of shares held in street name. As the beneficial owner of shares held for your account, you have the right to direct the registered holder to vote your shares as you instruct, and you also are invited to attend the Annual Meeting. Your bank, broker, plan trustee or other nominee has provided a voting instruction card for you to use in directing how your shares are to be voted. However, since a beneficial owner is not the shareholder of record, you may not vote your shares at the Annual Meeting, or any adjournment or postponement thereof, unless you obtain a legal proxy from the registered holder of the shares giving you the right to do so.

For directions on how to vote, please refer to the following instructions and those included on your proxy or voting instruction card.

Voting by Mail

Shareholders may submit proxies by completing, signing and dating their proxy or voting instruction card and mailing it in the envelope provided. If you do not timely return your proxy card, your shares will not be voted unless you or your proxy holder attends the Annual Meeting and any adjournment or postponement thereof and votes.

Voting by InternetPhone

Shareholders may submit proxies overvote by proxy by calling the Internet at https://www.cstproxy.com/onespaworld/2020 by following the instructionstoll-free number found on thetheir proxy or voting instruction card receivedcard.

Voting Online Prior to the Annual Meeting

Shareholders may vote by proxy by visiting www.proxyvote.com and entering the control number found in your Notice of Internet Availability. The availability of online voting may depend on the mail.voting procedures of the organization that holds your shares.

Voting Virtually During the Annual Meeting

Shareholders of record may vote virtually at the Annual Meeting with a proxy card by following the instructions at https://www.cstproxy.com/onespaworld/2020.www.virtualshareholdermeeting.com/OSW2021, entering the 16-digit control number found in your Notice of Internet Availability, and following the on-screen instructions. The availability of online voting may depend on the voting procedures of the organization that holds your shares. If you experience technical difficulties during the check-in process or during the meeting please call the support numbers provided on the registration page at www.virtualshareholdermeeting.com/OSW2021.

Your shares will be voted as you specifically instruct on your online ballot or as you specifically instruct on your proxy or voting instruction card. If you sign and return your proxy or voting instruction card, or complete your

If you do not provide timely instructions as to how your brokerage shares are to be voted, your broker will be prohibited from voting your shares on Proposal 1, Election of Class A Directors, Proposal 3, Approval of the Private Placement or Proposal 4, Approval of the Amended Articles.B Directors. These “brokernon-votes” will have no effect on determining the outcome of any of the proposals included herein.

If you hold shares as the shareholder of record, your vote by proxy must be received before the polls close at the Annual Meeting and any adjournment or postponement thereof. Voting and Internet voting end at 11:59 p.m., Eastern Daylight Time, on June 9, 2020.8, 2021.

If you hold shares as a beneficial owner, please follow the voting instructions provided by your bank, broker or other nominee.

You may change or revoke your vote at any time prior to the vote at the Annual Meeting.

If you are a shareholder of record, you may change your vote by granting a new proxy bearing a later date (which automatically revokes the earlier proxy), by sending a written notice of revocation to the address in Question 2423 prior to your shares being voted, or by attending the Annual Meeting. Attendance at the meeting will not cause your previously granted proxy to be revoked unless you specifically so request.

For shares you hold as a beneficial owner, you may change your vote by timely submitting new voting instructions to your bank, broker or other nominee (which revokes your earlier instructions), or, if you have obtained a legal proxy from the nominee giving you the right to vote your shares, by attending the Annual Meeting.

Attending the Annual Meeting

Shareholders of record will be able to attend the Annual Meeting online, vote their shares electronically and submit questions during the meeting by visiting https://www.cstproxy.com/onespaworld/2020. www.virtualshareholdermeeting.com/OSW2021. Holders of non-voting common shares of the Company as of the Record Date are entitled to listen in and to view the Annual Meeting and any adjournments thereof, and will have an opportunity to submit questions. Holders of non-voting common shares as of the Record Date are not entitled to vote with respect to the matters referred to herein, except Steiner Leisure shall be entitled to vote its non-voting common shares as of the Record Date in favor of the director nominee Marc Magliacano, the designated director of Steiner Leisure.

Beneficial Owner

Beneficial owners who wish to attend the virtual Annual Meeting must obtain a legal proxy by contacting their account representative at the bank, broker, or other nominee that holds their shares ande-mail a copy (a legible photograph is sufficient) of their legal proxy to proxy@continentalstock.com. Beneficial owners whoe-mail a valid legal proxy will be issued a meeting control number that will allow them to register to attend and participate in the Annual Meeting. After contacting Continental Stock Transfer & Trust Company, beneficial shareholders will receive ane-mail prior to the meeting with a link and instructions for entering the virtual meeting. Beneficial shareholders should contact Continental Stock Transfer & Trust Company at least five business days prior to June 10, 2020.that accompanied your proxy materials.

You may attend the Annual Meeting and any adjournment or postponement thereof only if you were a shareholder of record or a beneficial owner at the close of business on the Record Date, or you hold a valid proxy to vote at the Annual Meeting. Please see Question 2019 above for details on how to register for and attend the Annual Meeting.

The Annual Meeting will be held online on Wednesday, June 10, 20209, 2021 at 12:30 p.m., Eastern Daylight Time, at https://www.cstproxy.com/onespaworld/2020.www.virtualshareholdermeeting.com/OSW2021.

Due to the emerging public health threat of theCOVID-19 outbreak and to support the health and well-being of our shareholders, this year’s Annual Meeting will be held as a virtual meeting only. We believe that the virtual meeting format will provide better access and improved communication for both us and our shareholders, while providing shareholders with the same rights and opportunities to participate as they would have had at anin-person meeting.

Shareholder Proposals and Director Nominations

To be included in our proxy materials for next year’s annual meeting of shareholders, shareholder proposals must be received by our Secretary no later than January 22,December 30, 2021 and must be submitted to our Secretary at OneSpaWorld Holdings Limited, c/o One Spa World LLC, 770 South Dixie Highway, #200,Suite 200, Coral Gables, Florida 33146.

Proposals that are not timely submitted by January 22,December 30, 2021 or are submitted to the incorrect address or other than to the attention of our Secretary will be considered untimely and may, at our discretion, be excluded from our proxy materials. Shareholder proponents must also meet the requirements of Rule14a-8 of the Securities and Exchange Act, as amended (the “Exchange Act”), to be included in our proxy materials.

Shareholders who wish to (1) submit director nominees for inclusion in our proxy materials for next year’s annual meeting of shareholders or (2) present other items of business at next year’s annual meeting of shareholders must give written notice of their intention to do so in accordance with the deadlines described below

Our Class B Directors (serving until our 2021 annual meeting of shareholders)

Background of the Private Placement

The Board of Directors and the Company’s management regularly review and assess the Company’s operations and performance, financial condition and business strategy, and the various trends and conditions affecting the industry in which the Company operates in relation to the Company’s near- and long-term financial and strategic goals and plans.

Beginning in February 2020, the Company has experienced an unprecedented diminution in its financial position, liquidity and market capitalization from the effects ofCOVID-19 on the Company’s business, including, in particular, on the cruise industry on which the Company’s revenue is substantially dependent. In light of the Company’s near-term working capital and debt service requirements, to avoid a potential default under the Company’s existing credit facilities (as well as the potential acceleration of approximately $247.5 million of gross debt outstanding as of March 19, 2020), and to enhance the Company’s long-term financial position and ability to drive long-term growth, the Board of Directors began considering various strategic and financing alternatives in March 2020 as part of its regular review and assessment of the Company’s business and operations. Among other alternatives, the Board of Directors explored the possibility of obtaining additional debt financing from existing lenders, which were unwilling to consider extending additional debt to the Company given existing circumstances.

On March 20, 2020, the Company received an unsolicitednon-binding summary of proposed terms from Steiner Leisure for an investment in the Company. This proposal contemplated, among other things, (i) an investment of no less than $125 million in Common Shares at a per share price that represented a discount to the Company’sthree-day volume weighted average price per share (which implied a per share purchase price of approximately $2.61 as of the date of the proposal), (ii) the issuance of the Additional Shares, (iii) the right of Steiner Leisure to designate four directors to the Board of Directors, (iv) asix-month post-closing“lock-up” of the Common Shares to be acquired, and (v) certain other governance, information and other rights in favor of Steiner Leisure, including an uncapped expense reimbursement in favor of Steiner Leisure and its affiliates. In connection with the submission of the March 20, 2020 proposal and in anticipation of a potential proposed investment in the Company, Marc Magliacano, who is a director and officer of Steiner Leisure, recused himself from the Board of Directors’ evaluation of potential strategic and financing alternatives and the related process, including the evaluation of, and subsequent negotiation of, Steiner Leisure’s proposals and the Private Placement.

On March 21, 2020, in light of Steiner Leisure’s unsolicited proposal, the Board of Directors established a special committee, composed of Leonard Fluxman, Andrew R. Heyer, Walter F. McLallen, Jeffrey E. Stiefler and Stephen W. Powell (the “Special Committee”), to evaluate potential strategic and financing alternatives. After its formation, the Special Committee determined it was in the best interests of the Company and its shareholders to engage its own advisors to assist the Special Committee in evaluating, and to conduct a process on behalf of the Company to solicit, potential strategic and financing alternatives.

The Special Committee considered, and members of the Special Committee held discussions with, several potential financial advisors regarding their potential engagement to assist in an evaluation of potential strategic and financing alternatives for the Company. The Company subsequently engaged Nomura Securities International, Inc. (“Nomura”) as the Company’s financial advisor and placement agent to assist in such

evaluation and, if so determined by the Special Committee, to assist in the negotiation and consummation of any such transaction, and the Special Committee engaged Duff & Phelps as its financial advisor to advise, and to render an opinion to, the Special Committee regarding the fairness of any strategic transaction that the Special Committee identified as desirable to present to the Board of Directors for consideration. Duff & Phelps and Nomura were selected as financial advisors given, among other things, their respective qualifications, experience and reputation, and knowledge of and familiarity with the Company’s business and industry. Nomura was involved with the Company’s prior sale process and its business combination transaction and, based on that experience, was familiar with investors that had expressed interest in the Company in the past, and in a position to conduct potential investor outreach efforts in a targeted and expeditious manner. The Special Committee noted that Nomura previously served as a financial advisor to Steiner Leisure in connection with its sale of the Company and has provided services to Steiner Leisure and/or certain of its affiliates in connection with other matters, and engaged Duff & Phelps to provide an opinion regarding the fairness of any strategic transaction that it identified as desirable to present to the Board of Directors for consideration.

During late March and early April 2020, the Special Committee met telephonically several times with representatives of DLA Piper LLP (US) (“DLA”), counsel to the Special Committee and the Company for purposes of the potential strategic transaction, and Nomura to discuss the Company’s financial position, its near and long-term capital needs and funding strategy, the long-term prospects of the Company’s business and the effect of market and economic factors generally, Steiner Leisure’s March 20, 2020 proposal, and potential strategic and financing alternatives. At the Special Committee’s request, Nomura contacted 19 potential investors that were believed to potentially have interest in and the ability to provide the Company with the support needed. The potential investors included seven private equity firms, seven long-only investors, two hedge funds and three family offices / sovereign wealth funds. Among these potential investors, 14 parties agreed to be and were wall-crossed. Of the potential investors that were wall-crossed, eight parties requested and received presentations from the Company’s management. During the process, potential investors were advised of the Special Committee’s preference for a Common Share transaction as opposed to another investment structure given, among other things, the potential for material adverse tax consequences related to a preferred equity structure in certain circumstances.

Based on its unsolicited proposal and existing ownership in the Company, Steiner Leisure was one of the potential investors that was contacted and, like the other investors contacted, Steiner Leisure was asked to provide an indication of interest to the Company. At the Special Committee’s direction, Steiner Leisure was informed that certain aspects of its March 20, 2020 proposal would need to be improved in order for it to be considered. Ultimately, the Company received five proposals, including a revised proposal from Steiner Leisure on April 8, 2020 and the proposals described below that were received after entering into an exclusivity agreement with Steiner Leisure.

Steiner Leisure’s revised proposal contained improved economic and other terms relative to Steiner Leisure’s March 20, 2020 proposal. The revised proposal contemplated, among other things, an aggregate investment of $75 million in Common Shares at a per share price based on the lower of the10-day volume weighted average price per Common Share immediately before and after the signing (in each case, without a discount), which implied an upper limit on the per share purchase price of approximately $3.43 as of the date of the proposal. Steiner Leisure agreed to “back-stop” the full $75 million of the investment, but also indicated that it would provide other third-party investors with an opportunity to participate in up to $25 million of the issuance and that a portion of the Common Shares acquired by it would not be entitled to voting rights. The proposal also contemplated (i) the issuance of 9.9 million perpetual warrants exercisable for Common Shares (exercisable at 1.25x, 1.75x and 2.25x of the purchase price for the Common Shares acquired), (ii) the issuance of the Additional Shares, (iii) the right of Steiner Leisure to designate four directors to the Board of Directors, (iv) asix-month post-closing“lock-up” period with respect to the Common Shares acquired and (v) certain other governance, information and other rights in favor of Steiner Leisure and/or the other investors, as applicable, including an uncapped expense reimbursement in favor of Steiner Leisure. Steiner Leisure also expressed that it would not

require any further due diligence and would be ready, willing and able to quickly finalize and sign the definitive documentation for a potential transaction, which Steiner Leisure indicated that it believed was a key advantage to its proposal.

Following the Company’s receipt of these proposals, including Steiner Leisure’s revised proposal, the Special Committee met several times with representatives of DLA and Nomura to discuss and compare such proposals. The Special Committee then determined that, for the reasons, among others, described in the section entitled “The Board’s Reasons for Recommending Approval of the Private Placement,” it was in the best interests of the Company and its shareholders to continue discussions with Steiner Leisure regarding a potential transaction, which the Special Committee viewed, at that time, as the proposal that was most likely to result in a transaction that met the Company’s objectives, while also continuing discussions with other potential investors.

On April 20, 2020, after extensive negotiations with Steiner Leisure regarding its proposal and negotiations with other potential investors regarding alternative proposals, the Special Committee unanimously determined that it was in the best interests of the Company and its shareholders to enter into anon-binding indication of interest with Steiner Leisure. At the time, the Special Committee determined that the terms of the alternative proposals received were less favorable than those proposed by Steiner Leisure based on a number of considerations, including:

Thenon-binding indication of interest negotiated with Steiner Leisure contained further improved economic and other terms relative to Steiner Leisure’s April 8, 2020 proposal, including, among other things, (i) an increase in, and additional certainty with respect to, the proposed purchase price, (ii) a reduction in the number of warrants to be issued (from 9.9 million to 5 million) to Steiner Leisure and any other third-party investors (exercisable at 1.5x the purchase price for the Common Shares acquired) that would expire on the fifth anniversary of the closing of the transaction and would be redeemable by the Company if the trading price of the Common Shares exceeded $14.00 per share for any 20 trading days during any consecutive 30trading-day period, (iii) a requirement that one of the four Steiner Leisure Board designees would need to be reasonably acceptable to the disinterested Board of Directors, (iv) a12-month post-closing“lock-up” of the Common Shares acquired by Steiner Leisure and (v) a cap, to be mutually agreed upon, with respect to the expense reimbursement in favor of Steiner Leisure. Thisnon-binding indication of interest also contained a binding exclusivity period through April 30, 2020 for the parties to negotiate definitive transaction documents with respect to the proposed investment.

In March and April 2020, the Company engaged in discussions and negotiations with its lenders regarding potential amendments to the Company’s existing credit agreements in light of the Company’s financial position, potential defaults that may occur, as well as the potential acceleration of approximately $247.5 million of gross debt outstanding as of March 19, 2020 under such credit agreements, in the absence of such amendments and a potential equity investment by one or more third parties. During these discussions and negotiations, the Company’s lenders expressed their desire to only amend the Company’s existing credit agreements if a minimum amount of cash was invested in the Company’s equity by third-party investors.

Between April 22, 2020 and April 30, 2020, Kirkland & Ellis LLP (“K&E”), counsel to Steiner Leisure, and DLA exchanged, and the Special Committee and Steiner Leisure with the assistance of their respective advisors engaged in extensive negotiations regarding, drafts of the Investment Agreement and other definitive documents. Advisors to the third-partyco-investors also reviewed and provided comments to the Investment Agreement and other relevant definitive documents during this period.

On April 24, 2020, the Company received two unsolicited proposals from parties that had been contacted prior to the Company’s execution of its exclusivity agreement with Steiner Leisure. The Special Committee reviewed these proposals with the assistance of its legal and financial advisors and instructed Nomura, in accordance with the Company’s obligations under its exclusivity agreement with Steiner Leisure, to inform Steiner Leisure of the fact that the Company had received two unsolicited proposals with potentially more favorable terms than Steiner Leisure’s then-current proposal.

On April 26, 2020, following further negotiations, Steiner Leisure sent a revised proposal to the Company that contained improved economic and other terms relative to the previously agreednon-binding indication of interest, including, among other things, (i) an increase in the proposed purchase price of the Common Shares, (ii) an increase in the exercise price of the warrants, and (iii) a reduction in the number of directors that Steiner Leisure would be entitled to designate to the Board of Directors from four to three, with one nominee not subject to redesignation after the initial term thereof. The revised proposal also contemplated extending the exclusivity period through May 10, 2020, and indicated that its proposal would be withdrawn if it was not accepted on April 26, 2020. The Special Committee met to discuss and evaluate this revised proposal, and the two other unsolicited proposals in more detail, and determined that, for the reasons, among others, described in the section entitled “The Board’s Reasons for Recommending Approval of the Private Placement,” it was in the best interests of the Company and its shareholders to execute an amended and restatednon-binding summary with Steiner Leisure containing these revised terms, subject to Steiner Leisure agreeing to further improvements in its proposal, including a further increase in the exercise price of the warrants and an extension of the exclusivity period to May 3, 2020 (as compared to Steiner Leisure’s proposal of May 10, 2020). The Special Committee determined that the terms of the two unsolicited proposals were less favorable than those provided by Steiner Leisure based on a number of considerations, including:

In addition, the Special Committee considered the risk of Steiner Leisure abandoning the transaction if the Special Committee pursued the other alternative proposals. On April 27, 2020, after additional negotiations in which Steiner Leisure agreed to increase the exercise price and redemption price of the warrants and limit the extension of the exclusivity period, the Company (with the approval of the Special Committee) and Steiner Leisure executed an amended and restatednon-binding summary of proposed terms and extended the exclusivity period to May 3, 2020. The terms reflected in the amended and restatednon-binding summary of proposed terms reflected the material economic terms of the Private Placement, which were memorialized in definitive documentation over the course of the following days.

On April 29, 2020, the Special Committee and the Board of Directors (other than Mr. Magliacano, who previously had recused himself with respect to all Board of Directors’ matters related to the evaluation and negotiation of potential strategic and financing alternatives) met telephonically with representatives of DLA, Nomura and Duff & Phelps to discuss and consider the terms of the Private Placement. Representatives of Duff & Phelps presented certain financial analyses with respect to the financial terms of the Private Placement as summarized below under “Opinion of Financial Advisor to the Special Committee.” Representatives of Duff & Phelps then delivered Duff & Phelps’ oral opinion to the Special Committee, which opinion was confirmed by delivery of a written opinion dated April 29, 2020, as to the fairness of the Private Placement, from a financial point of view, to the Company. The full text of the written opinion of Duff & Phelps, dated April 29, 2020, which sets forth the assumptions made, procedures followed, and matters considered in connection with Duff & Phelps’ opinion, is attached asAppendix Ato this proxy statement and is incorporated by reference herein. After further discussion, the Special Committee unanimously determined that the terms of the Investment Agreement and the other transaction documents and the transactions contemplated thereby were advisable and in the best

interests of the Company and its shareholders, approved the terms of the Private Placement, and recommended its approval by the Board of Directors. The Board of Directors, based on the recommendation of the Special Committee, the opinion of Duff & Phelps and the other factors considered by the Special Committee, (i) unanimously approved the terms of the Private Placement, (ii) determined that the terms of the Investment Agreement and the other transaction documents and the transactions contemplated thereby were advisable and in the best interests of the Company and its shareholders, (iii) directed that the Private Placement be submitted to the shareholders of the Company for approval and (iv) recommended approval of Proposal 3 and Proposal 4 by the shareholders of the Company.

On April 29, 2020, the Company completed negotiations of and entered into amendments to the Company’s existing credit agreements. The continued effectiveness of these amendments is conditioned on the consummation of the Private Placement.

On April 30, 2020, the Company and the Investors executed the Investment Agreement.

The Board’s Reasons for Recommending Approval of the Private Placement

The Special Committee evaluated potential alternatives to the Private Placement during April 2020, and concluded that the Private Placement was in the best interests of the Company and its shareholders. In the weeks leading to the signing of the Investment Agreement, the Special Committee evaluated and negotiated the price, terms and conditions of the Private Placement, compared the price, terms and conditions of the Private Placement with other potential strategic and financing alternatives, consulted with the Company’s senior management and legal and financial advisors, and considered a number of factors. The various factors that the Special Committee considered that weighed positively in favor of the Private Placement included, among others and not necessarily in order of relative importance:

The Special Committee also considered a variety of risks and other potentially negative factors regarding the Private Placement. These factors included the following, which are not necessarily listed in order of relative importance:

The Special Committee concluded that the potentially negative factors associated with the Private Placement were outweighed by the potential benefits that it expected the Company would receive as a result of entering into the Private Placement. Accordingly, the Special Committee determined that the Private Placement was advisable and in the best interest of the Company and its shareholders.

The foregoing discussion of the factors considered by the Special Committee is not intended to be exhaustive, but, rather, includes the material factors considered by the Special Committee. In reaching their respective decision to approve the Private Placement and recommend its approval to the Company’s shareholders, the Special Committee and the Board of Directors did not quantify or assign any relative weights to the factors considered, and individual directors may have given different weights to different factors. The Special Committee unanimously recommended that the Board of Directors approve the Private Placement and recommend its approval to the Company’s shareholders, and the Board of Directors approved the Private Placement and recommends that the shareholders approve these proposals, in light of all these factors as a whole, and overall considers the factors to be favorable to, and to support, its determination.

Before voting on these proposals, shareholders should carefully read the “Cautionary Note Regarding Forward-

Looking Statements” section at the beginning of this proxy statement.

Opinion of Financial Advisor to the Special Committee

On April 29, 2020, Duff & Phelps rendered its oral opinion to the Special Committee of the Board of the Company (solely in their capacity as members of the Board) in connection with its consideration of the Proposed Transaction (which was subsequently confirmed in writing by delivery of its written opinion dated the same date) to the effect that, subject to the assumptions, qualifications, limitations and other matters considered by Duff & Phelps in connection with the preparation of its opinion, as of such date, the Proposed Transaction was fair from a financial point of view to the Company. In the portions of this proxy statement addressing the opinion, the term “Proposed Transaction” refers to the capital raise by the Company of approximately $75 million in exchange for Common Shares, warrants to purchase Common Shares, and modifications of the restriction period of the Company’s deferred shares.

The full text of Duff & Phelps’ opinion is included asAppendix Ato this proxy statement and describes the assumptions made, procedures followed, matters considered and limitations on the review undertaken by Duff & Phelps. The summary of Duff & Phelps’ opinion in this proxy statement is qualified in its entirety by reference to the full text of the opinion. The opinion was furnished for the use and benefit of the Special Committee in connection with its consideration of the Proposed Transaction and was not intended to be used for any other purpose, without Duff & Phelps’ express consent. Neither Duff & Phelps’ opinion nor the summary of its opinion and the related analyses set forth in this proxy statement is intended to be or constitutes a recommendation to any shareholder of the Company as to how such holder should act with respect to the Proposed Transaction.

Duff & Phelps’ opinion (i) did not address the merits of the underlying business decision to enter into the Proposed Transaction versus any alternative strategy or transaction, (ii) did not address any transaction related to

the Proposed Transaction, (iii) was not a recommendation as to how the Board or any shareholder should vote or act with respect to any matters relating to the Proposed Transaction, or whether to proceed with the Proposed Transaction or any related transaction, and (iv) did not indicate that the consideration received was the best possibly attainable under any circumstances; instead, it merely stated whether the consideration in the Proposed Transaction was within a range suggested by certain financial analyses. The decision as to whether to proceed with the Proposed Transaction or any related transaction may depend on an assessment of factors unrelated to the financial analysis on which Duff & Phelps’ opinion was based.

In connection with its opinion, Duff & Phelps made such reviews, analyses and inquiries as it deemed necessary and appropriate under the circumstances. Duff & Phelps also took into account its assessment of general economic, market and financial conditions, as well as its experience in securities and business valuation, in general, and with respect to similar transactions, in particular. Duff & Phelps’ procedures, investigations, and financial analysis with respect to the preparation of its opinion included, but were not limited to, the items summarized below:

Assumptions, Qualifications and Limiting Conditions

In performing its analyses and rendering its opinion with respect to the Proposed Transaction, Duff & Phelps, with the Company’s consent:

To the extent that any of the foregoing assumptions or any of the facts on which Duff & Phelps’ opinion is based prove to be untrue in any material respect, the opinion cannot and should not be relied upon. Furthermore, in Duff & Phelps’ analysis and in connection with the preparation of its opinion, Duff & Phelps made numerous

assumptions with respect to industry performance, general business, market and economic conditions and other matters, many of which are beyond the control of any party involved in the Proposed Transaction.

Duff & Phelps prepared its opinion effective as of the date of such opinion. Duff & Phelps’ opinion was necessarily based upon market, economic, financial and other conditions as they existed and could be evaluated as of the date of the opinion, and Duff & Phelps disclaimed any undertaking or obligation to advise any person of any change in any fact or matter affecting its opinion which may come or be brought to the attention of Duff & Phelps after the date of the opinion.

Duff & Phelps’ opinion noted that the credit, financial and stock markets had been experiencing unusual volatility. In rendering its opinion,Duff & Phelps expressed no opinion or view as to any potential effects of such volatility on the Company or the Proposed Transaction.

Duff & Phelps’ opinion further noted that, in January 2020, the World Health Organization declaredCOVID-19 to constitute a “Public Health Emergency of International Concern” and that given the uncertainty of the current situation regardingCOVID-19, the duration of any business disruption and related financial impact with respect to the Company or the Proposed Transaction could not be reasonably estimated as of the date of such opinion. In rendering its opinion,Duff & Phelps expressed no opinion or view as to any potential effects ofCOVID-19 on the Company or the Proposed Transaction.

Duff & Phelps did not evaluate the Company’s solvency or conduct an independent appraisal or physical inspection of any specific assets or liabilities (contingent or otherwise). Duff & Phelps was not requested to, and did not, (i) initiate any discussions with, or solicit any indications of interest from, third parties with respect to the Proposed Transaction, the assets, businesses or operations of the Company, or any alternatives to the Proposed Transaction, (ii) negotiate the terms of the Proposed Transaction, and therefore, Duff & Phelps assumed that such terms were the most beneficial terms, from the Company’s perspective, that could, under the circumstances, be negotiated among the parties to the Investment Term Sheet and the Proposed Transaction, or (iii) advise the Board or any other party with respect to alternatives to the Proposed Transaction.

Duff & Phelps did not express any opinion as to the market price or value of the Company’s common shares (or anything else) after the announcement or the consummation of the Proposed Transaction. Duff & Phelps’ opinion should not be construed as a valuation opinion, credit rating, solvency opinion, an analysis of the Company’s or any other party’s credit worthiness, as tax advice, or as accounting advice. Duff & Phelps did not make, and assumed no responsibility to make, any representation, or render any opinion, as to any legal matter.

In rendering its opinion, Duff & Phelps did not express any opinion with respect to the amount or nature of any compensation to any of the Company’s officers, directors, or employees, or any class of such persons, relative to the consideration in the Proposed Transaction, or with respect to the fairness of any such compensation.

Summary of Material Financial Analyses by Duff & Phelps

Set forth below is a summary of the material financial analyses performed by Duff & Phelps in connection with providing its opinion to the Special Committee of the Board of the Company. While this summary describes the analyses and factors that Duff & Phelps deemed material in its presentation to the Special Committee of the Board of the Company, it is not a comprehensive description of all analyses and factors considered by Duff & Phelps. The preparation of a fairness opinion is a complex process that involves various determinations as to appropriate and relevant methods of financial analysis and the application of these methods to the particular circumstances. Therefore, neither its opinion nor Duff & Phelps’ underlying analysis is susceptible to partial analysis or summary description. In arriving at its opinion, Duff & Phelps did not attribute any particular weight to any analysis or factor considered by it, but rather made qualitative judgments as to the significance and relevance of each analysis and factor. Accordingly, Duff & Phelps’ analyses must be considered as a whole and selecting portions of its analyses and of the factors considered by it in rendering its opinion, without considering

all analyses and factors, could create a misleading or incomplete view of the evaluation process underlying its opinion. The conclusion reached by Duff & Phelps was based on all analyses and factors taken as a whole, and also on the application of Duff & Phelps’ own experience and judgment.

The financial analyses summarized below include information presented in tabular format. In order for Duff & Phelps’ financial analyses to be fully understood, the tables must be read together with the text of each summary. The tables alone do not constitute a complete description of the financial analyses undertaken by Duff & Phelps. Considering the data below without considering the full narrative description of the financial analyses, including the methodologies and assumptions underlying the analyses, could create a misleading or incomplete view of Duff & Phelps’ financial analyses.

Selected Precedent Transactions Analysis. Duff & Phelps performed an analysis of selected PIPE transactions that Duff & Phelps deemed relevant. The selected transactions were chosen because they involved common equity raises within the last five years for companies in similar situations as the Company, as evidenced by the companies’ leverage at the time of the transaction announcement based on total debt to total capital; the companies’ publicly traded stock price one day prior to announcement of the transaction as a percent of the52-week historical high publicly traded stock price; and the size of the investment as a percent of the companies’ market capitalization one day prior to the announcement of the transaction. Duff & Phelps analyzed the discount or premium of the offering price per share in the selected transactions relative to the following publicly traded stock price metrics prior to the announcement date: (i) thefive-day volume weighted average price (“VWAP”); (ii) the stock price one day prior to announcement; (iii) the stock price five days prior to announcement; and (iv) the stock price ten days prior to announcement.

In order to compare the discount per share offered in the Proposed Transaction to that of the selected transactions, Duff & Phelps adjusted the purchase price per share of $4.00 for the impact of the warrants issued as part of the Proposed Transaction to arrive at an effective purchase price per share. Duff & Phelps arrived at an estimated warrant value per underlying share using a Black-Scholes option pricing model, which resulted in a value of $1.67 per warrant. Duff & Phelps then multiplied the value per warrant by five million warrants, which resulted in an aggregate warrant value of approximately $8.3 million, and then divided the aggregate warrant value by the number of shares being issued in the Proposed Transaction, or 18.75 million shares. This analysis resulted in an estimated warrant value per share of $0.45 and an estimated effective purchase price per share of $3.55. For valuation purposes, Duff & Phelps considered the deferred shares to be issued and outstanding because the Company had apre-existing obligation to issue such deferred shares and such shares were treated, under GAAP, as being issued and outstanding for purposes of the Company’s financial statements. In considering the impact of the modifications of the restriction period of the Company’s deferred shares, Duff & Phelps did not view such modifications as reducing the aggregate equity value of the Company and, therefore, did not consider it in evaluating the purchase price per share. As of April 28, 2020, the effective purchase price per share represented the following: (i) a discount to thefive-day VWAP of approximately 20.4%; (ii) a discount to the stock price as of the market close one day prior to announcement of approximately 23.4%; (iii) a discount to the stock price as of the market close five days prior to announcement of approximately 7.7%; and (iv) a discount to the stock price as of the market close ten days prior to announcement of approximately 11.3%.

The selected transactions, and corresponding financial data for the selected transactions, were:

in one or more respects, including the nature of the business and financial performance economics. Duff & Phelps reviewed the enterprise value as a multiple of latest twelve months (“LTM”) of earnings before interest, taxes, depreciation, and amortization (“EBITDA”).

Enterprise value means, generally, the value as of a specified date of the relevant company’s outstanding equity securities (taking into account outstanding options and other securities convertible, exercisable or exchangeable into or for equity securities of the company), plus the amount of debt outstanding, preferred stock andnon-controlling interests, and less the amount of cash and cash equivalents on its balance sheet. Enterprise values used in the selected public companies analysis were calculated using the closing price of the common shares of the selected companies as of April 28, 2020 and, with respect to the Company, Duff & Phelps selected a range of LTM EBITDA multiples of 9.0x to 10.0x.

The selected public companies, and corresponding financial data for the selected public companies were:

Source: S&P Capital IQ, SEC Filings, Annual

Leadership Structure

Our Board of Directors is responsible for establishing and Interim Reportsmaintaining an effective leadership structure for the Company. Our Board of Directors has not mandated a particular leadership structure, and thus maintains the flexibility to determine on an individual basis whether the positions of Chief Executive Officer and Executive Chairman of the board (the “Chairman of the Board”) should be combined or separated. This flexibility allows our Board of Directors to organize its functions and conduct its business in a manner it deems most effective based on the current circumstances. As of March 31, 2021, Leonard Fluxman serves as Executive Chairman, Chief Executive Officer and Director. Together, Mr. Fluxman and Stephen Lazarus (our Chief Operating Officer and Chief Financial Officer) lead a senior management team with over 130 years of combined industry experience. Previously, Glenn Fusfield was the Chief Executive Officer and Leonard Fluxman served as the Executive Chairman. Steven J. Heyer is our designated Lead Independent Director.

The selected public companies analysis resulted in a range of enterprise valuesBoard believes that having Mr. Fluxman serve as both Chairman and Chief Executive Officer is the most effective leadership structure for the Company basedat this time, particularly with respect to managing the ongoing impact of COVID-19 on LTM EBITDAour business, operations, results of operations and financial condition, and the Company’s resumption of normalized operations as the pandemic subsides. Mr. Fluxman has over 30 years of February 29, 2020leadership and operations experience, including over 25 years of $55.9 million,experience in the consumer and consumer-related products and services industry. Mr. Fluxman served as Steiner Leisure’s Chief Executive Officer from January 2001 to March 2019. The Board believes that he is uniquely well positioned to lead our business, operations and strategy at this time.

The combination of $502.9 millionthe Chief Executive Officer and Chairman roles at this time enables consistent communication and coordination with our team members throughout the Company and with our Board of Directors, and effective and efficient implementation of our business strategies. The combination of the Chief Executive Officer and Chairman roles is balanced by our Lead Independent Director position, by the independence of all of our other directors, each of whom has significant experience in leadership roles at public companies and other large, complex organizations, and by the three principal committees of the Board, each of which consists solely of independent directors.

Directors (collectively, the “Co-Investors” and, together with Steiner Leisure, and its affiliates required to be paid or reimbursed by the Company pursuant to the Investment Agreement) by July 15, 2020, which may be extended to July 31, 2020 under certain circumstances, (ii)“Investors”). Pursuant the Investment Agreement, has been terminated by the Company or any other party thereto or (iii) the Investment Agreement shall have been amended, amended and restated, supplemented or otherwise modifiedwe completed a private placement financing transaction on June 12, 2020 (the “2020 Private Placement”) in a manner the effect of which, shall be to reduce the minimum investment amount to an amount less than $65 million. In the event that the Private Placement does not occur and, as a result, the Credit Agreement Amendments are not effective, the Company may not be in compliance with certain representations, warranties and affirmative covenants under its existing credit agreements, which would, absent an agreement from the Company’s existing lenders, result in a default under these existing credit agreements and the potential acceleration of approximately $247.5 million of gross debt outstanding as of March 19, 2020.

Proposal 3: Approval of the Private Placement for purposes of Nasdaq Listing Rule 5635

Background and Overview

Please refer to “Background of the Private Placement” and “The Board’s Reasons for Recommending Approval of the Private Placement” above for information with respect to the background and overview of, and the reasons for, the Private Placement.

Description of the Investment Agreement

Overview

The Investment Agreement provides that, prior to the closing of the Private Placement, and assuming shareholder approval of Proposals 3 and 4, the Company will authorize a new class ofNon-Voting Common Shares by adopting the Amended Articles. At closing of the Private Placement, pursuant to the Investment Agreement, the Company will, among other things, (i) issuewe issued to Steiner Leisure an aggregate of (x) approximately 15.0 millionNon-Votingnon-voting Common Sharescommon shares and (y) warrants to purchase approximately 4.0 millionNon-Votingnon-voting Common Sharescommon shares at an exercise price of $5.75 per share, and (ii) issuewe issued to theCo-Investors an aggregate of (x) approximately 3.7 million voting common shares of the Voting Common Shares and (y) warrants to purchase approximately 1.0 million Voting Common Sharesvoting common shares at an exercise price of $5.75 per share, for an aggregate purchase price of $75.0 million.

In addition, the Investment Agreement provides that, in consideration for, among other things, Steiner Leisure providing a “back stop” for the Private Placement and Steiner Leisure’s agreement to voting limitations in respect of certain of the securities issuable to it, the Company will issue and deliver an aggregate of 5.0 million Common Shares to Steiner Leisure at the closing of the Private Placement (collectively, the “Additional Shares”), which will satisfy in full the Company’s obligation to issue 5.0 million “deferred” Common Shares to Steiner Leisure pursuant to Section 2.6 of the Business Combination Agreement, dated as of November 1, 2018 (as amended, supplemented or otherwise modified from time to time in accordance with its terms, the “BCA”).

Conditions to the Closing of the Private Placement

The obligations of the Company and the Investors to close the Private Placement are subject to the satisfaction or waiver (to the extent permitted by law) by the Company and amajority-in-interest of the Investors (based on the number of Company securities to be issued to such Investors) (the “Majority of the Investors”) at or prior to the closing of the Private Placement of each of the following conditions, among other customary conditions:

The obligation of the Company to close the Private Placement is subject to the satisfaction or waiver (to the extent permitted by law) by the Company at or prior to the closing of the Private Placement of each of the following conditions, among other customary conditions:

The obligations of the Investors to close the Private Placement are subject to the satisfaction or waiver (to the extent permitted by law) by the Majority of the Investors at or prior to the closing of the Private Placement of each of the following conditions, among other customary conditions:

The obligation of Steiner Leisure to close the Private Placement as between the Company and Steiner Leisure is subject to the satisfaction or waiver (to the extent permitted by law) by Steiner Leisure at or prior to the closing of the Private Placement of each of the following conditions, among other customary conditions:

The obligation of Neuberger Berman Alternative Funds, Neuberger Berman Long Short Fund and NB All Cap Alpha Master Ltd. (collectively, “Neuberger Berman”) to close the Private Placement as between the Company and Neuberger Berman is subject to the satisfaction or waiver by Neuberger Berman at or prior to the closing of the Private Placement of the following condition: the closing of the purchase by Steiner Leisure of no less than $50approximately $6.4 million of Common Shares and warrants prior to or simultaneously with the purchase by Neuberger Berman.

Assuming the applicable conditions to closing have been satisfied or waived, the closingoffering-related expenses, resulting in total net proceeds of the Private Placement with respect to Steiner Leisure will occur even if aCo-Investor does not or is unable to close its portion of the Private Placement.

None of the parties to the Investment Agreement may rely on the failure of any condition set forth above to be satisfied if such failure was proximately caused by such party’s failure to use reasonable best efforts to cause the applicable closing of the Private Placement to occur or a breach of the Investment Agreement.

Termination

The Investment Agreement may be terminated at any time prior to the closing of the Private Placement by mutual written consent of the Company and the Majority of the Investors.

The Investment Agreement may also be terminated by either the Company or the Majority of the Investors in certain customary circumstances, including if:

The Investment Agreement may also be terminated by the Majority of the Investors if:

Neuberger Berman may terminate the Investment Agreement with respect to its purchase thereunder in the event of a termination of the Investment Agreement by Steiner Leisure.

Assuming the applicable conditions to closing have been satisfied or waived, the termination of the Investment Agreement by anyCo-Investor or by the Company with respect to anyCo-Investor will not affect the ability of the Company and Steiner Leisure to close Steiner Leisure’s portion of the Private Placement. Upon a termination of the Investment Agreement with respect to anyCo-Investor or any failure by theCo-Investor to close its portion of the Private Placement, Steiner Leisure may elect to acquire the Common Shares (in the form ofNon-Voting Common Shares) and warrants to acquire Common Shares (in the form of Non-Voting Common Shares) that suchCo-Investor would otherwise have acquired.

Upon a termination of the Investment Agreement in accordance with its terms, and subject to the limitations set forth therein, (i) neither the Company nor the Investors will have any further liability or obligation with respect to the Investment Agreement, except for liability for fraud or any material and willful breach by any party and (ii) the Company may be required to reimburse the fees, costs and expenses of Steiner Leisure and its affiliates incurred in connection with the Private Placement (subject to a cap of $1.25 million) in certain circumstances.

No Solicitation

The Investment Agreement containsnon-solicitation provisions that prohibit the Company and its representatives from, among other things, directly or indirectly initiating, soliciting or encouraging, or facilitating, any offer or proposal from any person or group which constitutes, or could reasonably be expected to result in, an alternative transaction to the Private Placement or an inquiry with respect to such a transaction. In addition, the Company has agreed to certain covenants in support of the Private Placement, including that the Board of Directors recommend that the Company’s shareholders adopt and approve the Investment Agreement and approve the transactions contemplated by the Investment Agreement and other related agreements.

Transaction Support

At the Company shareholders’ meeting to approve Proposal 3 and Proposal 4, eachCo-Investor that beneficially owns any Common Shares as of the date of the Investment Agreement (such Common Shares, collectively, the “Covered Shares”) has agreed to, among other things, (i) appear at such meeting for quorum purposes, (ii) vote all Covered Shares in favor of Proposal 3 and Proposal 4 and (iii) vote all Covered Shares that would oppose or impede the approval of Proposal 3 and Proposal 4.

EachCo-Investor has also agreed not to deposit the Covered Shares into a voting trust or enter into any voting or similar agreement with respect to the Covered Shares.approximately $68.6 million.

Steiner Leisure Director Designation Right

Under the terms of the Investment Agreement, Steiner Leisure will havewas granted the right to designate and appoint three directors to the Company’s board of directors at the closing of the Private Placement, with two of these directors being Class C directors and the other director being a Class B director. One of the Class C director seats willis not be subjectto re-designation by Steiner Steiner Leisure at the expiration of the initial term thereof under the Governance Agreement.

Representations and Warranties

In the Investment Agreement, each of the Company and the Investors made certain customary and limited representations and warranties. Certain “fundamental” representations and warranties of the Company and the Investors under the Investment Agreement survive until the first anniversary of the closing of the Private Placement.

Covenants

The Company has agreed to certain customary covenants in the Investment Agreement restricting the conduct of its business between the date of the Investment Agreement and the earlier of the closing of the Private Placement and the termination of the Investment Agreement in accordance with its terms.

Pursuant to the Investment Agreement, the Company applied to cause the Common Shares to be issued in connection with the Private Placement to be approved for listing on Nasdaq, subject only to official notice of issuance.

In addition, pursuant to the Investment Agreement, the Company and the Investors have agreed to certain other customary covenants, including, among other things, (i) preparing and filing the proxy statement with respect to and seeking shareholder approval of the Private Placement, (ii) using their respective reasonable best efforts to consummate the Private Placement as promptly as practicable and (iii) submitting the required filings under the HSR Act to the U.S. Federal Trade Commission and the Antitrust Division of the U.S. Department of Justice.

Transfer Restrictions

Following the closing of the Private Placement, the Investors (other than Neuberger Berman) mayBerman Group LLC) are not able to transfer the purchased Common Sharescommon shares and warrants until the twelve-month anniversary of such closing, subject to customary exceptions (e.g., transfers to affiliates).

Description ofNon-Voting Common Shares

See Proposal 4 for a description of the rights, preferences and privileges of theNon-Voting Common Shares.

Description of Warrants

The warrants issuable pursuant to the Investment Agreement will expire on the earlier of (i) the fifth anniversary of the closing of the Private Placement or (ii) the Redemption Date (as defined below). The warrants will be

immediately exercisable by the holder thereof upon payment of the purchase price; provided, however, that the holder may exercise such warrants on a “cashless” basis, in accordance with a specified formula. In addition, the Company may, at any time prior to their expiration, elect to redeem not less than all of such then-outstanding warrants at a price of $0.01 per warrant, provided that the last sales price of the Common Shares reported has been at least $14.50 per share (subject to adjustment in accordance with certain specified events), on each of twenty trading days within the thirty-trading day period ending on the third business day prior to the date on which notice of the redemption is given (the “Redemption Date”), and provided that the Common Shares issuable upon exercise of such warrants have been registered, qualified or are exempt from registration or qualification under the Securities Act of 1933, as amended (the “Securities Act”) and under the securities laws of the state of residence of the registered holder of the warrant. The warrants to be issued to Steiner Leisure pursuant to the Private Placement will initially be exercisable solely forNon-Voting Common Shares.

Governance Agreement

Designation RightsAudit Committee

Contingent upon shareholder approvalAt least annually, our Audit Committee reviews and assesses its charter and its performance under the charter. In addition, our Audit Committee has, among others, the following authority and responsibilities:

Our Audit Committee charter requires that each of the members of our Audit Committee is independent, as defined under SEC rules and the Nasdaq Listing Rules, and that each member is able to read and understand fundamental financial statements, including balance sheet, income statement, statement of equity and statement of cash flows. Additionally, at least one member of our Audit Committee will have past employment experience in finance or accounting, professional certification in accounting, or other comparable experience or background resulting in the individual being financially sophisticated, which may include being or having been a chief executive officer, chief financial officer or other senior officer with financial oversight responsibilities, and at least one member of the Committee must be an audit committee financial expert. The authority and responsibilities of our Audit Committee are described in greater detail in our Audit Committee charter, available on our website at www.onespaworld.com/investor-relations.

Our Audit Committee consists of Mr. McLallen (chairperson), Mr. Powell and Mr. A. Heyer. Mr. McLallen qualifies as an “audit committee financial expert” as that term is defined by the applicable SEC regulations and has employment experience in finance or accounting, requisite professional certification in accounting, or other comparable experience or background as required by the Nasdaq Listing Rules. Each of our Audit Committee members is “financially literate” as that term is defined by the Nasdaq Listing Rules and our Board of Directors has determined that each is independent pursuant to applicable SEC regulations and the Nasdaq Listing Rules. Our Audit Committee held eight meetings during the fiscal year ended December 31, 2020.