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                                                                    EXHIBIT 5.01

PLATO Learning, Inc.
10801 Nesbitt Avenue South
Bloomington, Minnesota 55437


         Re: 200,000 Shares of Common Stock, $0.01 par value, of PLATO
Learning, Inc.

Ladies or Gentlemen:

         We refer to the Registration Statement on Form S-8 (the "Registration
Statement") filed by PLATO Learning, Inc. (the "Company") with the Securities
and Exchange Commission pursuant to the Securities Act of 1933, as amended (the
"Securities Act"), relating to the registration of 200,000 shares of Common
Stock, $0.01 par value (the "Shares"), of the Company which may be issued from
time to time upon exercise of stock options granted to employees of the Company
pursuant to the PLATO Learning, Inc. 2000 Non-Employee Directors Stock Option
Plan (the "Plan").

         We are familiar with the proceedings to date with respect to the Plan
and the proposed issuance and sale of the Shares and have examined such records,
documents and questions of law, and satisfied ourselves as to such matters of
fact, as we have considered relevant and necessary as a basis for this opinion.

         Based on the foregoing, we are of the opinion that:

         1. The Company is duly incorporated and validly existing under the
laws of the State of Delaware.

         2. The Shares will be, as and when acquired in accordance with the
terms and conditions of the Plan, legally issued, fully paid and non-assessable
under the Delaware General Corporation Law.

         We do not find it necessary for the purposes of this opinion to cover,
and accordingly we express no opinion as to, the application of the securities
or blue sky laws of the various states to the sale of the Shares.

         We hereby consent to the filing of this opinion as an Exhibit to the
Registration Statement and to all references to our firm included in or made a
part of the Registration Statement.

                                               Very truly yours,


                                               Winston & Strawn