The film's plot is based primarily 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 (book)).
PlotPooh visits the wooden bridge where he stumbles upon a fir cone and accidentally drops it in the river. After discovering that the cone went under the bridge, Pooh invents the game Poohsticks.
Later, when Pooh, Piglet, Rabbit, and Roo are playing Pooh-sticks, they notice Eeyore floating in the river. Pooh suggests to use stones to get Eeyore out to shore, which surprisingly works. Then Eeyore claims that he was in the river due to getting bounced. Tigger, who bounces by, claims that he actually coughed on Eeyore, but Mr. Narrator reveals that he did bounce Eeyore.
Pooh follows Eeyore to his gloomy place to ask what's wrong. Eeyore believes that everyone forgot about his birthday. Pooh decides to help out and plans to give Eeyore a jar of honey, but he ends up eating it. With the help of Owl, the empty pot turns into a greeting pot with love from Pooh. Then Owl flies to tell Christopher Robin about Eeyore’s many happy returns of the day. Piglet had a big red balloon ready for Eeyore, but he pops it.
The gang throws a surprise party for Eeyore. A short time later, Tigger bounces by and haves Rabbit’s piece of cake. Rabbit disapproves of this and wants him to leave. Christopher Robin decides to have a game of Pooh-sticks to settle this. Eeyore wins most of the games and Tigger won none at all. Causing him to conclude that "Tiggers don't like Pooh-sticks". Eeyore's secret for winning, as he explains to Tigger afterwards, is to "let his stick drop in a twitchy sort of way." As Tigger bounces Eeyore again, Christopher Robin, Pooh and finally Piglet all decide that "Tigger’s all right, really."
Winnie the Pooh and a Day for Eeyore made it into The Many Adventures of Winnie the Pooh along with Winnie the Pooh and the Honey Tree, Winnie the Pooh and the Blustery Day and Winnie the Pooh and Tigger Too. It is the fourth segment in the film.
- Hal Smith as Owl and Winnie the Pooh
- Ralph Wright as Eeyore
- John Fiedler as Piglet
- Paul Winchell as Tigger
- Will Ryan as Rabbit
- Kim Christianson as Christopher Robin
- Julie McWhirter as Kanga
- Dick Billingsley as Roo
- Laurie Main as Mr. Narrator
The featurette made its video debut in 1984 with the compilation VHS, Winnie the Pooh and Friends. It is added as a fourth featurette on the VHS, DVD, and Blu-Ray Pack of The Many Adventures of Winnie the Pooh.