Prospectus Supplement Filed Pursuant to Rule 424(b)(3) (To Prospectus dated October 12, 2000) Registration Number 333-44960 $805,000,000 Diamond Offshore Drilling, Inc. Zero Coupon Convertible Debentures Due June 6, 2020 ------------------------------------------- This prospectus supplement relates to the resale by the holders of our Zero Coupon Convertible Debentures Due June 6, 2020 and the shares of our common stock issuable upon the conversion of the debentures. This prospectus supplement should be read in conjunction with, and may not be delivered or utilized without, the prospectus dated October 12, 2000. The terms of the debentures are set forth in the prospectus. The information in the table appearing under the heading "Selling Securityholders" in the prospectus is amended by adding the information below with respect to persons not previously listed in the prospectus and by superceding the information with respect to persons previously listed in the prospectus that are listed below. PRINCIPAL AMOUNT AT NUMBER OF MATURITY OF DEBENTURES PERCENTAGE OF CONVERSION BENEFICIALLY OWNED DEBENTURES SHARES THAT NAME THAT MAY BE SOLD OUTSTANDING MAY BE SOLD - ---- ---------------- ----------- ----------- Protective Life Insurance Company............................ $ 20,000,000 2.48% 172,150 Morgan Stanley Dean Witter Convertible Securities Trust...... $ 6,000,000 0.75% 51,645 The Northwestern Mutual Life Insurance Company (1) .......... $ 13,000,000 1.61% 111,897 Bankers Trust Company as trustee for Daimler Chrysler Corp Employee No. 1 Pension Plan............................... $ 3,470,000 0.43% 29,868 Franklin and Marshall College................................ $ 235,000 0.03% 2,022 Penn Treaty Network America Insurance Company................ $ 280,000 0.03% 2,410 State Street Bank as custodian for GE Pension Trust.......... $ 1,715,000 0.21% 14,761 Lutheran Brotherhood......................................... $ 5,000,000 0.62% 43,037 IL Annuity & Insurance Company............................... $ 30,000,000 3.73% 258,225 Hamilton Partners Limited.................................... $ 53,000,000 6.58% 456,197 Pacific Life Insurance Company............................... $ 20,016,000 2.49% 172,287 Lehman Brothers Inc.......................................... $ 10,940,000 1.36% 94,166 Potlatch-First Trust Co. of St. Paul......................... $ 1,200,000 0.15% 10,329 Standard Insurance Company................................... $ 650,000 0.08% 5,594 Key Trust Convertible Securities Fund........................ $ 315,000 0.04% 2,711 EB Convertible Securities Fund............................... $ 1,900,000 0.24% 16,354 Charitable Convertible Securities Fund....................... $ 2,000,000 0.25% 17,215 Parker Hannifin Pension/Key.................................. $ 400,000 0.05% 3,443 Omnova Solutions............................................. $ 120,000 0.01% 1,032 Aerojet Inc. Foundation...................................... $ 65,000 0.01% 559 Any other holder of Debentures or future transferees from any such Holder (2).......................................... $ 156,101,000 19.39% 1,343,639 Total........................................................ $ 805,000,000 100.00% 6,929,013 (3) - ---------------------------- (1) Includes $1,000,000 principal amount held in The Northwestern Mutual Life Insurance Company Group Annuity Separate Account. (2) Information concerning other selling holders of Debentures will be set forth in prospectus supplements from time to time, if required. (3) The conversion shares do not total 6,929,038 shares due to rounding resulting from the elimination of fractional shares. -------------------------------------- The date of this prospectus supplement is November 9, 2000. 2