When Tigger spreads a rumor that Pooh is leaving the Hundred Acre Wood, everyone throws Pooh a good-bye party. Pooh then leaves and stays for a second, but when he gets home, he finds Eeyore living at his home.

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 and the gang pretend to be in the Wild West during a play.

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.

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

When Tigger breaks a mirror Rabbit was using, Rabbit believes he has bad luck, and so do the others, but it turns out Tigger has the bad luck.

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

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.

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.

Rabbit makes a law that there will be no more Valentine's Day after everyone has received countless valentines in previous years.

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

Pooh believes he can no longer enjoy honey when he loses his "sweet tooth," which has been stolen by pack rats.

The gang is in a state of panic because they think they are being haunted by a ghost which was just Piglet running scared silly.

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

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.

Pooh and Piglet help a young heffalump who is having difficulty learning trapping from his father.

Tigger takes on the identity of "The Masked Offender" in order to help people, but causes more trouble than he fixes.

When the gang discovers that Tigger has never had a birthday, they decide to throw him a party that fails to impress him, especially when he does not get what he wants. A trip to the Hundred-Acre-Wood's wishing well leads Tigger to "Wishland," where everything he desires comes true. Eventually, though, he must choose between all of the possessions he has gained and his friends.

Christopher Robin gives Piglet "magic earmuffs" to help give him confidence in his ice skating. After losing the earmuffs, Piglet has a crisis of belief, only to discover his own skill when he must save the gang from the perils of an icy river.

Sick of his friends ruining his garden while they are playing pirate, Rabbit gives them a fake treasure map "drawn from his great-great-great uncle and the greastest rabbit pirate ever, Long John Cottontail" that leads them to a chest full of rocks. When he becomes worried that his friends will hate him for deceiving them, he tries to get the chest back before they open it.

Pooh gets stuck in a bubble, Gopher's hole blows away in a storm, and Rabbit hosts a vegetable meeting.

It is Groundhog Day but there is no groundhog, so Rabbit makes Piglet the groundhog and he changes the holiday.

Rabbit builds a fortress to prevent anyone from trampling into his garden only to realize that he has forgotten to put a door, thus trapping himself inside.