- Ben Zachary as Winnie the Pooh
- Rachel Zachary as Darby
- Cash Zachary as Christopher Robin
- Johnny Portugal as Owl
- Zeb Rawlins as Piglet
- Mattilda Zachary as Kanga
- Charlie Rawlins as Roo
- Abe Kelsey as Tigger
- Hagar Rawlins as Porcupine
- Georgia Rawlins as Mama Heffalump
- Jude Rawlins as Rabbit
- Andy Zachary as Gopher
- Lost Bird as Dexter
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