Produced by Rick Reinert's unit and animated by former Disney animators, Ennis McNulty, Dave Bennett, Nancy Beiman, Irv Anderson, Spencer Peel, Virgil Ross, Ken O' Brien, Tom Ray, and Lars Hult, this was the first Disney animated film since the 1938Silly Symphonies short Merbabies to be produced by an outside studio. (The company had also previously produced the educational Disney short, Winnie the Pooh Discovers the Seasons in 1981).
The films plot is primarily based on two A.A. Milne stories: "In which Pooh invents a new game and Eeyore joins in" (Chapter 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 racing game out of it. As the game uses sticks instead of cones, he calls the game "Poohsticks".
Sometime later, while Pooh, Piglet, Rabbit, and Roo are playing "Poohsticks", they see Eeyore floating in the river below. After a somewhat successful attempt to get him to the shore, he tells them that he fell in due to being bounced from behind. When Tigger arrives on the scene, he claims that his bounce was actually a cough, leading to an argument between him and Eeyore, but with some outside help from the narrator, the animals find out that Tigger has indeed deliberately bounced Eeyore on page 245. Tigger says it was all a joke, but nobody else feels that way. Tigger disgustedly says they have no sense of humor, and bounces away.
As Eeyore seems particularly depressed this day, Pooh follows him and asks what's wrong. Eeyore answers that he's unhappy because it's his birthday, and nobody has taken any notice to celebrate it. Pooh decides to give him a jar of honey, but 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 misspelled greeting on the pot and then flies off to tell Christopher Robin about the birthday. Piglet has planned to give a balloon to Eeyore, but when Owl greets him from the sky, he forgets to look where he was going, until he bumps into a tree and accidentally causes it to pop.
Piglet is very sad that his gift for Eeyore is spoiled, but he presents it to him anyway, and only a minute later, Pooh brings the empty pot. Eeyore is gladdened, as he can now put the broken balloon into the pot and remove it again. Pooh and his friends then pitch in and plan a surprise party for their friend.
During the party, Tigger arrives and helps himself to the festivities. This angers Rabbit, who opines that Tigger should leave because of the way he treated Eeyore before. Roo wants Tigger to stay, and Christopher Robin's solution is for everyone to go to the bridge and play Poohsticks. Eeyore, a first-time player, wins the most games out of everyone, while Tigger does not win at all. Eeyore's secret for winning, as he explains to Tigger afterwards, is to "let [his] stick drop in a twitchy sort of way." Christopher Robin, Pooh and Piglet decide that "Tigger's all right, really."
Note: On DVD and Blu-Ray releases of The Many Adventures of Winnie the Pooh, the short carries different voice credits than those on previous video releases. Jim Cummings (Pooh/Tigger), Ken Sansom (Rabbit), Tress MacNeille (Kanga), Trevyn Savage (Christopher Robin), Andre Stojka (Owl), Peter Cullen (Eeyore), Steve Schatzberg (Piglet), and Aaron Spann (Roo) are listed, despite that the original soundtrack (with Smith, Winchell, etc.) appears unaltered. This could imply that a re-dub was attempted with these actors, but ultimately was unused.
This is the first and only Winnie the Pooh short not to have a song at the end.
While the classic opening sequence and theme is utilized, the audio is completely re-recorded and re-arranged, with the theme sung in the key of G major instead of F major, and the opening narration now spoken by Laurie Main (instead of the late Sebastian Cabot). The cuckoo clock sound effect was also redubbed as well.