List of Anniversary Playboy Playmates
- 55th Anniversary (January 2009): Dasha Astafieva
- 50th Anniversary (January 2004): Colleen Shannon
- 45th Anniversary (January 1999): Jaime Bergman
- 40th Anniversary (January 1994): Anna-Marie Goddard
- 35th Anniversary (January 1989): Fawna MacLaren
- 30th Anniversary (January 1984): Penny Baker
- 25th Anniversary (January 1979): Candy Loving
- 20th Anniversary (January 1974): Nancy Cameron
- 15th Anniversary (January 1969): Leslie Bianchini
- 10th Anniversary (December 1963): Donna Michelle
- 5th Anniversary (December 1958): Joyce Nizzari
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