The film's title is a play on the slogan "Tippecanoe and Tyler too" made famous during the 1840 United States presidential election.

It featured the voices of Sterling Holloway as Winnie the Pooh, Paul Winchell as Tigger, John Fiedler as Piglet, Timothy Turner as Christopher Robin, Dori Whitaker as Roo, Barbara Luddy (in her final film role) as Kanga, Junius Matthews (in his final film role) as Rabbit, and Sebastian Cabot as Mr. Narrator.

Pooh, Piglet, and Rabbit execute the plan the next morning, and while they manage to lose Tigger, things soon go wrong when the three get lost and are unable to find their way home.

After Rabbit separates from Pooh and Piglet due to a disagreement on how to escape, the latter two manage to find their way out of the forest on their own before running into Tigger, who had already found his way out.

Pooh and Piglet soon discover Tigger and Roo in the tree and recruit Christopher Robin, Kanga, and Rabbit to help get them down.