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This was the only Winnie-the-Pooh film where Jeff Bennett provided Piglet's and Christopher Robin's singing voice. It is also the first Winnie-the-Pooh film where Owl is absent, and the first Winnie-the-Pooh film that Carly Simon is involved in. It is also the series finale of The New Adventures of Winnie the Pooh.
- Jim Cummings as Winnie the Pooh and Tigger
- John Fiedler as Piglet
- Ken Sansom as Rabbit
- Kath Soucie as Kanga
- Peter Cullen as Eeyore
- Nikita Hopkins as Roo
- Michael Gough as Gopher
- William Green as Christopher Robin
- Michael York as Mr. Narrator
- Paul Winchell as Tigger's flashback voice (Winnie the Pooh and Christmas Too sequence)
- Edan Gross as Christopher Robin's flashback voice (Winnie the Pooh and Christmas Too sequence)
- Jeff Bennett as Piglet and Christopher Robin's singing voices
- Frank Welker as Bugs in Rabbit's flashback (Winnie the Pooh and Christmas Too sequence)