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.

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.

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.

When Pooh knocks an eggshell out of tree, the gang becomes convinced that the sky is falling.

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'.

On a stormy night, Piglet enters a world where he is a brave Knight.

Tigger's disastrous inventions bother his friends.

When an adult Kessie returns to the Hundred-Acre Wood, Rabbit still treats her like a fledgling. When Kessie tries to prove that she is an adult, she runs away, but gets kidnapped by Stan and Heff, who demand honey for her release.

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.