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

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.

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 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.

Piglet, Tigger and Rabbit go on a hunt to capture crows and leaves Pooh to watch Rabbit's garden. Unbeknownst to them the whole thing is a setup just to leave the garden under the protection of the "nitwit" Pooh.

After Tigger tells the gang a scary story about "the Grab Me-Cotcha", they are alarmed to find that Pooh and Piglet are finding the honeymoon and comes home

Pooh tells the story of the three little pigs, Hundred Acre Wood style.

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.

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.

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

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

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

Eeyore becomes sick of his tail, so he abandons it. But Eeyore decides he wants it back, and Detective Tigger helps him. But the others find it and claim it as an object of their own.

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.

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

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.

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

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

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.

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 is stuck in the treehouse until he jumps off. Gopher tries to make Pooh faster so he won't be late as often.

Pooh thinks he has misplaced Piglet and tries to find him until he found him somewhere

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.

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

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

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

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

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

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

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

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?

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

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.

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

Pooh and his friends look for the April Fool, not aware that it is Christopher Robin playing jokes on them.

Rabbit becomes annoyed when Gopher starts digging his 'Ultimate Tunnel' around his house, so he re-writes the equation when Pooh accidentally messed it up, but that makes things worse.

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.

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

Pooh is babysitting Owl's nephew, Dexter, and Roo. They and the rest of the gang are invited to Christopher Robin's house so they could see his science project, which is an insect. But the gang accidentally lets the bug loose and soon agree that they will find a replacement bug for Christopher Robin.

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.

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

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

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.

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.

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.