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.

A game gets out of hand when Pooh accidentally touches Gopher's Big Boulder exhibition.

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

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

Christopher Robin and the gang are playing 'war' in their bedroom. His mother tells him to tidy up, so Pooh and his friends explain why they are playing 'war'.

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

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.

Owl wants to see his family, so Pooh and Piglet organise a family reunion for him. But does Rabbit think they're true?

Rabbit has no more work to do around his house and garden, so he leaves Pooh and the others to watch over. But while Rabbit is gone, Pooh and the others create utter chaos in his house and garden.

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.

Eeyore agrees to help Rabbit plant a seed near Eeyore's house. But Eeyore thinks that his seed will not grow, so Pooh and Tigger disguise Piglet as a flower and leave him near Eeyore's house overnight. When Rabbit thinks Eeyore is a better gardener than him because of the disguised Piglet, Rabbit gives up his property to Eeyore and lives in Eeyore's house. However, Eeyore is an inexperienced gardener and soon messes up Rabbit's garden.

It is a dark and stormy night in the Hundred Acre Wood and Tigger spins a tale of the mad scientist Piglet and his monster Frankenpooh.

When Pooh and Christopher Robin are playing pirates, Christopher Robin makes up a treasure map, and puts it in a bottle. He gives it to Pooh, but it gets stolen by the pack rats, so Pooh and the gang try to get it back to Christopher Robin.

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.

Piglet gets hiccups, so the gang helps Piglet to cure his hiccups

When Pooh loses his appetite, the others think he's not Winnie the Pooh, and then everybody thinks neither one of them are themselves. So, Detective Pooh and Tigger go look for Pooh's appetite.

Piglet has a bad dream about losing his friends in the storm and becomes afraid to go to sleep. All of his friends except him blow away. Will Piglet ever have a good dream?

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

Piglet finds a shadow, and takes it home. His friends get somewhat jealous. That night the shadow leaves and Piglet goes to find him.

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.

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

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.