This was the only Winnie-the-Pooh film where Jeff Bennett provided Piglet's and Christopher Robin's singing voice. It is also the first Winnie-the-Pooh film where Owl does not appear at all, and the first Winnie-the-Pooh film that Carly Simon is involved in
The story begins on Christmas Eve, where Winnie the Pooh is carrying a Christmas tree back to his home. After saying hi to the Narrator, the tree gets stuck in the front door, forcing him to push it in. The tree lands in a honey pot, and after Pooh balances it out, he slips off the tree and breaks a shelf with a present that he made for Piglet. When Piglet suddenly arrives, Pooh tries to hide his present. Because the broken shelf can't stay up anymore, Pooh is forced to find a different hiding spot. Rabbit, Tigger, Gopher, Kanga, and Roo arrive and wonder which Pooh isn't answering the door. After a long search, he finally puts the present in an empty honey pot and helps himself to a full honey pot, feeling so satisfied that he forgets to answer the door. Meanwhile, his annoyed friends are still wondering why Pooh won't open the door. Roo suggests opening the door themselves, revealing Pooh eating honey. Although surprised, they proceed to prepare the decorations for the Christmas tree. Eeyore then arrives while they decorate the tree with ornaments, honey cookies (which Pooh is tempted to eat them), and a star for the top of the tree. Tigger dances around with jingle bells, briefly annoying Rabbit until he joins in on the fun. That night, Roo wonders if Santa is coming. The others claim that he is as he had received their letter. Piglet recalls what had happened during the time when he nearly didn't. Rabbit then tells Roo the story of Winnie the Pooh and Christmas Too which explains of how their letter failed to reach Santa and that Pooh dressed up as Santa to bring gifts to his friends, but was unsuccessful. After a second failed attempt to deliver their letter, he returns with the bad news, but his friends say that he is more important than presents until Christopher Robin arrives with their presents.
After the story ends, Pooh (who's dressing as Santa again) appears with a sack of gifts for everyone. The next day, it was Christmas and everyone heads outside to have fun. Roo enjoys his new sled (a wooden board) while Pooh plays in the snow. They come across Rabbit, who is collecting firewood and sends Eeyore to take a load of firewood back to Pooh's house (Pooh and Roo disappear after this point). Rabbit sees Tigger in the distance with jingle bells, forcing Rabbit to hide, but fails to avoid him. Tigger constantly teases Rabbit with the jingle bells, forcing Rabbit to take them from him. Tigger allows Rabbit to borrow them, who then throws them into a tree stump. Meanwhile, Piglet gives Pooh some honey pots as a Christmas present. Pooh suddenly remembers Piglet's present and begins searching his home, but forgets where he hid it. His search went from Christmas Day to New Year's Eve. Pooh then hears Christopher Robin calling for him and he goes to find him. After finding him with a box of party decorations, he reveals that he is preparing a party for everyone to celebrate New Year's Eve. Pooh suggests having the party at Rabbit's house and he heads there with the party decorations.
At Rabbit's house, Rabbit and Piglet are tending to Rabbit's potted carrot. While Rabbit goes to get the plant food, Piglet gets startled by a knock on the door and he hides under Rabbit's bed with the carrot. Pooh suddenly comes in and gets interested with the honey in Rabbit's cupboard. Rabbit closes the cupboard, unwittingly pushing Pooh inside and is shocked to find that his carrot is gone. After hearing a noise coming from the cupboard, he opens it and finds Pooh inside, helping himself to some honey, much to Rabbit's annoyance. After finding Piglet under the bed with the carrot, he hears another knock on the door, which turns out to be Tigger, who bounces on him. Eeyore suddenly pops out from under them. Tigger then tries to demonstrate an ability where he throws a snowball and then catches it himself, but he misses it and flies into Rabbit's house. Rabbit worries about his carrot and although it is unharmed, he is more annoyed with Tigger's antics. Pooh then announces the party that Christopher Robin is hosting at Rabbit's house. While Tigger enjoys the moment, Rabbit doesn't. When Tigger tries to decorate the place, he ends up making a mess, making Rabbit so angry that he throws everyone out, planning to move. While they wonder what to do to keep Rabbit from leaving, Pooh suggests doing a resolution (which Christopher Robin had told him about earlier), a promise that they must keep no matter what.
Tigger ties a rock to his tail to keep him from bouncing. Piglet then decides to bounce like Tigger to ensure that he won't feel afraid, but in response Tigger starts acting scared. Pooh also starts acting gloomy while Eeyore starts acting like Pooh (eating honey, standing on two legs, and wearing a red shirt that identical to Pooh's). Rabbit proceeds to leave until his four friends return with their changed personalities, which immediately makes Rabbit leave. While traveling, Rabbit suddenly slips and falls down a cliff. After catching his carrot, he sees his suitcase flying through the air and landing on the other side of the log that Rabbit is standing on, sending him flying.
While his friends search for Rabbit, they find him stuck in a tree with bees attempting to abduct him. The four then regain their old personalities and Tigger rescues Rabbit. After realizing that they broke their promises, they knew they had to say goodbye to Rabbit, but he claims that they don't need to and they don't have to change since he likes them how they are (also admitting that he's the one that needs to change). Christopher Robin arrives and a now changed Rabbit agrees to have the party at his house. The party begins with everyone (except Owl) at Rabbit's house celebrating New Year's Eve. Rabbit gives Tigger back the jingle bells he took from him and apologizes to him, but Tigger forgives him. Pooh finally remembers where he left Piglet's gift and goes home to get it. After returning with a honey pot, he takes Piglet's present out of it, which is revealed to be a music box. After singing a song to Piglet following the music, Piglet loved the gift and claims that Pooh is a greater gift, ending the story.Ken Sansom as Rabbit
Jim Cummings as Winnie the Pooh and Tigger
Peter Cullen as Eeyore
John Fiedler as Piglet
William Green as Christopher Robin
Nikita Hopkins as Roo
Kath Soucie as Kanga
Michael Gough as Gopher
Michael York as The Narrator
Paul Winchell as Tigger (Winnie the Pooh and Christmas Too sequence)
Jeff Bennett as Piglet and Christopher Robin (singing voice)
The film was released as a direct-to-DVD on November 12, 2002. The film was released for the first time on Blu-ray on November 5, 2013 as the "Gift of Friendship Edition", the same day as the 30th Anniversary Blu-ray release for the 1983 animated featurette Mickey's Christmas Carol.