The beginning of the story is interrupted by Tigger, who was tired of hear most of the stories about Pooh and slams the book closed. The narrator asks him of who should the story be about as the book reopens. Tigger claims that he knows someone that is good (he is talking about himself) and attempts to change the title page which causes him, the pieces of the title page, and the book to fall. Tigger puts the book back up and rearranges the letters such as ripping a W and an N, putting the THE on a different spot, makes a new picture for the title page, turn the two O's into lower case g's, and giving the word Tigger some color and the story continues. While trying to find somebody to play with, Tigger gleefully bounces around the Hundred Acre Wood, disrupting his friends' attempts to prepare for the winter and accidentally causing a huge rock to fall on Eeyore's house. Rabbit leads the others in trying to remove it with an elaborate pulley system but Tigger intervenes, knocking the rock away with his Whoopty-Dooper-Loopty-Looper-Alley-Ooper bounce which wrecks the machine and getting everyone covered in mud and Rabbit becomes angry at him for ruining everything because of his habit of bouncing. Feeling alone, Tigger sulks on a bridge and Roo, trying to cheer him up, asks if there are other Tiggers. Fascinated by the idea, Tigger talks to Owl, who explains about family trees while Tigger puts some paintings that he knocked over back up. Tigger, taking this literally, heads out to find a huge stripey tree and, after not finding one, return to Tigger's house. He then demestrates the bounce the results him bouncing off a hammack, rolling around a record player, spinning on a string of lanterns, going through a basketball net, flying out the window and hitting a branch, and bouncing across the room. Roo later tries it, and hits the same hammack, record player, and string of lanterns from before, lands on a ball, launched on a springy stool, and flies into a closet where they find a heart-shaped locket in which Tigger thinks his family's picture is inside it. After he uses a sword to open it, they relieze its empty. Roo suggest that Tigger should write them a letter and he does so. After he finishes the letter, he lets the wind take it, hoping it would reach his family. No reply comes and Tigger feels more alone then ever. Meanwhile Pooh, Piglet, and Eeyore find frogs which have stripes and bounce, but were not Tiggers. The trio later find some bees that also have stripes and after Pooh tries to get honey from their hive, the bees give chase that results the bees throwing them into the air every time they run about a yard.That night, the first night of winter, everybody else gathers at Piglet's house. Feeling sorry for Tigger, Roo announces that they should write a letter to him. Everyone adds a bit of friendly advice before signing "your family" at the bottom of the page. Roo then slips the letter into Tigger's letter box. The next day, everybody is woken by Tigger, who brandishes the letter. He shouts joyfully that his family has written to him and also that they are coming to visit the next evening. They are all shocked, as they had never written down anything that even resembles that; nevertheless, Tigger replies that he always reads between the lines and the other weren't able to tell him the truth. Later, Roo gathers Pooh, Piglet, Owl, and Eeyore over to his home. He and his mother Kanga say they are going to charade as fellow Tiggers to attend the party and make Tigger feel loved. They are halfway through making the costumes when Rabbit bursts through the door, telling them that they should be gathering supplies (or should already have) for the impending snowstorm. Meanwhile, Tigger is preparing for his party when somebody rings the doorbell. He opens the door to reveal a large number of Tiggers (his friends) who claim to be his family.A party ensues with drinks, dance and games, and all the while Tigger falls for it. Yet when Roo attempts the Whoopty-Dooper Loopty-Looper Ally-Ooper Bounce where he flies around the room, smashes into the same hammack from before, crashes into some balloons, falls on a chair, and is launched into the closet again and his mask falls off, the others reveal themselves as Tigger's friends. Tigger is dejected and angry after realizing that he is the one and only Tigger in the Hundred Acre Wood and that his friends lied to him and leaves, saying "TTFE, Ta-ta forever!!" and takes the letter and locket with him. He hikes through the snow, slips on a frozen lake, and falls down a cliff until he finds a large tree on the cliff side which matches the description he gave of his family tree (A giant pine tree with the snow giving the illusion of Tigger stripes). He bounces across the branches and finds nothing, so he sits there, heartbroken and drops his letter.Meanwhile, Pooh, Roo, Piglet, and Eeyore mount an expedition to find Tigger. They ask Rabbit to lead them, who initially refuses, but reluctantly agrees after seeing how much they miss their friend, especially Roo. When they find his letter they see him up in the tree in which he mistakens them for his family, they tell him to return home, with Rabbit saying he should "Forget about all this other Tiggers nonsense". infuriating Tigger, but when a sudden avalanche caused by his irate shouting occurs, he pulls them all out of trouble. Unfortunately, Tigger himself is still caught in the avalanche. Roo remembers the Whoopty-Dooper Loopty Looper Ally-Ooper bounce and travels down through the rock and snow to Tigger and wakes him from unconsciousness. To get out of the avalanche, they perform the signature bounce together, dodge chucks of ice in the air, and fly through a log just before a stone smashes into it. When the avalanche ends, everyone tells Christopher Robin why Tigger left, Christopher tells Tigger he did not have to leave to find his family. Tigger objects and reaches for his letter that, until recently, he thought to be from his family, but finds it missing and thinks he lost it in the avalanche (unaware that he lost it earlier) and doesn't remember what it says. It is not until Owl, Kanga, Roo, Eeyore, Pooh, and Piglet recite the letter for him that he realizes that they sent the letter, not his family. Hearing this, Tigger finally comes to realize what was true all along, that his family is right here and always has been: his friends. Once they return home, Tigger gives everyone gifts: Eeyore gets a new house (the guest house meant for Tigger's "Family"), Pooh gets lots of Honey, Piglet gets a stack of firewood, Christopher Robin was given a toy plane, Owl was given a yo-yo, Kanga gets a hat, and Rabbit is promised that he will watch where he's going. Lastly, he gives Roo his heart pendant, but it is still empty. Christopher Robin remedies this by taking a picture of Tigger's "family". The film ends with the camera slowly zooming back from the picture in the locket as it closes.
- Baloo, Bagheera, King Louie, and the characters guest star in this film.