The film's plot is based primarily on two A. A. Milne stories: "In which Pooh invents a new game and Eeyore joins in (Story VI from "The House at Pooh Corner") and "In which Eeyore has a Birthday and Gets Two Presents" (Chapter VI of Winnie the Pooh) ".
The story begins with Pooh taking a walk to a wooden bridge over a river where he likes to do nothing in particular. On this particular day, though, he finds a fir cone and ends up dropping it in the river. Noticing that, due to the flow of the river, the cone went under the bridge, Pooh decides to make a game out of it, calling it Poohsticks.
Sometime later, while Pooh, Piglet, Roo, and Rabbit are playing Poohsticks, they see Eeyore floating in the river below. After a somewhat successful attempt to get him to shore, he tells them that he fell in due to being bounced from behind. Tigger shows up suddenly, and Rabbit fingers Tigger for bouncing Eeyore into the river. Despite Eeyore's postivie assumption that Tigger bounced him, Tigger denies it, claiming that he actually coughed. The narrator, however, steps in and, by turning back to an earlier page in the story, confirms that Tigger did bounce Eeyore after all. Disgusted, Tigger leaves, but Eeyore returns to where he had been sitting, feeling more gloomy than usual.
Pooh follows him and asks what's wrong. Eeyore answers that he's unhappy because it's his birthday, and there's nobody around to celebrate it with him. Offering to help, Pooh hurries back home and tells Piglet that they have to find presents to give to Eeyore. Piglet runs back to his house to get a big red balloon, while Pooh picks out a jar of honey from his cabinet. But Pooh doesn't get far before he has a hunger attack and ends up eating the honey. Upon realizing this, he decides to ask Owl for help. Owl writes a birthday greeting on the pot and then flies off to tell Christopher Robin.
Meanwhile, Piglet accidentally trips while carrying the balloon, causing it to pop. He is upset that his gift for Eeyore is no longer good, but he presents it to the donkey anyway. Eeyore doesn't mind, though, since he likes it this way, and later, Pooh brings the empty pot, which Eeyore uses as a storage device for the balloon. Later that day, Christoper Robin throws a birthday party for Eeyore, which Tigger crashes. Afterwards, they all play a game of Poohsticks, which Eeyore (who had never played before) ends up winning more times than the others (especially Tigger, who did not win at all, and afterwards declares that "Tiggers don't like Poohsticks!") After everyone goes home, Eeyore shares his secret for winning at Poohsticks with Tigger (when you drop the stick, drop it in a twitchy sort of way), and gets bounced again. Meanwhile, Christopher Robin, Pooh and Piglet have all decided that "Tigger's all right, really".
- Hal Smith as Winnie the Pooh and Owl
- Andre Stojka as Owl (Soundtrack Only)
- Jim Cummings as Winnie the Pooh and Tigger (Soundtrack Only)
- Ralph Wright as Eeyore
- Peter Cullen as Eeyore (Soundtrack Only)
- Paul Winchell as Tigger
- John Fiedler as Piglet
- Steve Schatzberg as Piglet (Soundtrack Only)
- Will Ryan as Rabbit
- Ken Sansom as Rabbit (Soundtrack Only)
- Kim Christianson as Christopher Robin
- Trevyn Savage as Christopher Robin (Soundtrack Only)
- Julie McWhirter Dees as Kanga
- Tress MacNeille as Kanga (Soundtrack Only)
- Dick Billingsley as Roo
- Aaron Spann as Roo (Soundtrack Only)
- Narrated by Laurie Main