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                                                                    EXHIBIT 5.01

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


                  Re:  700,000 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 700,000 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 Stock Incentive 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