Piglet, feeling sorry for Eeyore, who always seems to be depressed, convinces the others to spend a whole day trying to cheer him up.

Strange things happen when Christopher Robin and the gang watch a late night "Slusher" film.

Christopher Robin, Pooh and the gang have to look after a dog.

When Tigger loses control of Christopher Robin's toy train, he and Pooh are put on trial as train robbers.

After Christopher Robin and the gang accidentally break a statue of his great-grandfather while cleaning up, Christopher runs away from home, with the gang offering their homes for him. When it turns out that he can not live in any of their houses, Pooh and the gang build him a home.

When Gopher receives a large shovel, he goes overboard "improving" everyone's home.

When the gang throw a birthday party for Pooh, they become convinced he is old and wise when they see how many candles there are on his cake. When they all ask Pooh for advice, things go awry.

Tigger causes trouble when he intrudes on Piglet's poetry.

Owl's poor singing upsets Rabbit, but scares off the crows.

When Christopher Robin has to attend a "grown up" girl's party, Pooh and the gang become afraid he, too, will grow up and will forget them.

Tigger befriends a cloud that keeps crying. Pooh and his friends try to let Tigger do his bouncing lessons so the cloud responds to Tigger so it can be friendly.

Gopher's Grandpappy comes for a visit, prompting Gopher to try to accomplish his Grandpappy's life-long dream of building an above-ground underground city.

As a reward for Christopher Robin eating all his vegetables, he along with Pooh, Piglet, and Tigger go to the theater to watch Birdzilla, a scary monster movie. During the film, Piglet gets scared and thinks the movie is real and the monster will get him. The gang tries to convince him that it is only make-believe and proceed to make their own monster film to prove it.

Pooh has been borrowing too much honey from Rabbit lately. This makes Rabbit mad to the point where he says that Pooh is "eating him out of house and honey". Desperate, Pooh and his friends try to retrieve honey from a beehive, so Rabbit will not have to move away. Nevertheless, this proves to be a daunting task.

When the gang goes camping, Piglet is frightened by Tigger's stories and comes up against one of his greatest fears: Heffalumps.

Pooh borrows a balloon from Christopher Robin and the gang all panics when Rabbit causes it to become deflated.

Rabbit rescues a little bird named Kessie and finds himself in the role of parent. His overly-protective tendencies cause trouble when Kessie begins to feel an urge to fly, which Rabbit expressly forbids for fear of losing her.

Piglet sets out with Tigger and Rabbit to the Land of Milk and Honey, hoping to get some honey for Pooh as a gift after Piglet gets an unexpected gift from Pooh. They discover a tiny race of Piglet lookalikes called "Piglies" who elect Piglet their king, which causes him internal conflict--especially when Tigger and Rabbit abuse the Piglies' hospitality.

Tigger encourages Christopher Robin to clean his messy room by throwing everything he owns under the bed. This proves troublesome when the gang discovers that the evil Crud and his sneezing minion, Smudge occupy a land beneath the mattress and plan to spread messiness everywhere.

All the honey in the Hundred-Acre Wood has disappeared and it appears to be the work of a Heffalump and a Woozle named Heff and Stan. When the gang successfully recovers the honey, Stan decides to get backup in the form of a giant Woozle named Wooster--but Pooh's offer of friendship provides a surprising resolution to the conflict.

When Rabbit forces Tigger to have a bath, the bounce-happy tiger's stripes come off. The gang believes that this "new" creature isn't Tigger, as all Tiggers have stripes, prompting an identity crisis in the sad tiger. Eventually, Eeyore solves the problem by pointing out that it is Tigger's heart, not his stripes, that make him who he truly is.

The gang meets a wind-up monkey toy named Bruno, who claims to be the "best toy a kid could get," in Christopher Robin's closet. Bruno boasts that he is better than all of Christopher's old toys, making them fear that they will be replaced.

Christopher Robin and the gang get into mischief while a babysitter tries to look after them.

After a calendar mishap leads Rabbit to believe that his birthday has been forgotten, he decides to run away from the Hundred-Acre-Wood, only to found by a secondhand shop owner who puts him up for sale. While the gang tries to find Rabbit, the bunny himself must fend off some thuggish toys who are out to make trouble.

After being buffeted about by the wind, Piglet becomes afraid of going outside.