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.

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

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

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.

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

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

When Rabbit throws away a lone bunny-shaped bookend, it finds its way all around the gang.

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.

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.

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.

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.

When Christopher Robin shows Pooh a wishing star, Pooh tells Piglet, Tigger and Rabbit about it, and they all wish for something. But, when Pooh thinks he wished out the wishing star, and that the others' wishes will not come true, he tries his best to fulfill them all.

Tigger thinks his great uncle is a lion and declares himself, "King of the Beasties" with chaotic results.

Pooh and the gang try to deal with the pack rats during a flood.

Piglet saves Tigger's life, and Tigger becomes Piglet's servant.

When the gang finds a pile of feathers on the trail, they believe that they belonged to Owl and that he has gone bald.

Piglet thinks he is too small and moves away from the Hundred Acre Wood.

Rabbit is at his wit's end when Gopher is forced to move in with him.

Rabbit gives Tigger weighted shoes and challenges him to jump the highest rock in the wood to keep him out of the way.

When Rabbit takes Gopher's flashlight without asking, Gopher panics and he and the rest of the gang go in search of it.

Eeyore dresses up like Tigger in order to become more popular.

When Owl reads a thrilling mystery novel to the gang, Tigger inadvertently helps him find his lost glasses, prompting the bird to declare Tigger a detective. The bouncy tiger likes the idea, but resorts to committing crimes in secret to give himself cases to solve, which leads to attack of conscience when Pooh is accused of stealing honey.

Rabbit wants to plan a party for his five hundred visiting bunny relatives, and becomes obsessed with using a schedule to keep Pooh, Piglet, and Tigger on track. But when his excessive scheduling ends up driving everyone away by accident, he realizes that his desire for order has kept his family and friends from having fun.

Roo asks Tigger to keep him from having a bath, and the tiger recruits Piglet to switch places with Roo to trick Kanga. But when Roo and Tigger get excessively dirty, and Kanga pretends that she does not recognize Piglet, everyone realizes that their attempted "switcheroo" has gone too far.