During the fall, Tigger has been bouncing on anyone he comes across for fun, especially Rabbit when he is gardening, which angers Rabbit, so he calls a meeting with Pooh and Piglet and formulates a plan to prevent Tigger from bouncing: abandon Tigger in the woods, and find him the next day so hopefully Tigger will stop bouncing on his friends unexpectedly. Initially the plan seems to work, but when Rabbit, Pooh, and Piglet cannot find their way home, Pooh makes a suggestion about following a sandpit in order to find their way out of the forest. In an attempt to prove Pooh wrong, Rabbit wanders away. Pooh and Piglet then fall asleep, but are woken by Pooh's empty stomach. He explains to Piglet that his honeypots have been calling to his tummy from home and that he couldn't hear them over Rabbit's voice. Pooh and Piglet find their way out of the forest, but are immediately bounced by Tigger. Piglet, realizing that the plan failed, mentions Rabbit's plan, and Tigger goes into the forest to find him. Rabbit walks through the forest by himself, and is scared by numerous noises such as a caterpillar eating a leaf and frogs croaking. Rabbit tries to run away in a panic, only to be tackled by Tigger. Rabbit is humiliated that his plan to lose Tigger had failed. Tigger explains to him that "Tiggers never get lost", and takes Rabbit home.
In the next chapter, wintertime comes and Roo wants to go play. Kanga cannot be with him so she calls on Tigger to look after Roo as long as he comes back in time for Roo's nap. Tigger gladly accepts. Along the way through the woods, Tigger and Roo see Rabbit skating on the ice. Tigger tries to teach Roo how to ice skate by doing it himself, but unfortunately, he loses his balance and collides with Rabbit while trying to regain it. In moments Tigger slides into a snowbank and Rabbit crashes into his house. Tigger then decides that he does not like ice skating. Later on, while bouncing around the woods with Roo on his back, Tigger accidentally jumps to the top of a very tall tree and is afraid to climb back down. He gets even more scared when Roo uses his tail as a swing, making Tigger think he's "rocking the forest".
Meanwhile, Pooh and Piglet are investigating strange animal tracks that are actually Tigger and Roo's. Suddenly, they hear Tigger howling, for help and quickly hide. At first, Pooh mistakes Tigger's howl for the sound of a "Jagular"; but after seeing that it is actually Tigger and Roo in the tree, he and Piglet come to the rescue. Shortly afterward, Christopher Robin, Rabbit, and Kanga arrive and the gang uses Christopher's coat as a net for Tigger and Roo to land in once they jump from the tree. Roo successfully jumps down, but Tigger, who is still too frightened to move, makes up several excuses to not come down. Rabbit then decides that the group will just have to leave Tigger in the tree forever, on which Tigger promises never to bounce again if he ever is released from his predicament. At that moment, the narrator chimes in for help. Tigger begs him to "narrate" him down from the tree, and he tilts the book sideways, allowing Tigger to step onto the text of the page. Tigger starts to feel better that he made it this far but before he can do otherwise, the narrator tilts the book back the other way, causing Tigger to fall into the snow.
Happy, Tigger attempts to bounce but Rabbit stops him reminding Tigger of the promise he made. Devastated, Tigger realizes he cannot bounce anymore and slowly walks away and Rabbit feels better that there will be peace, but everyone else does not and felt sad to see Tigger depressed and remind Rabbit of the joy Tigger brought when he was bouncing. Then Rabbit shows sympathy for Tigger and takes back the promise they had agreed on; he is then given a friendly tackle by an overly-excited Tigger. Tigger invites everyone to bounce with him and even teaches Rabbit how to do it. For the first time, Rabbit is happy to be bouncing, as is everyone else as Tigger sings his signature song once more before the short closes.
In 1975, Winnie the Pooh and Tigger Too won the Grammy Award for Best Album for Children (this fact is mentioned during the pop-up facts during the film as a bonus feature for the 2002 DVD release of The Many Adventures of Winnie the Pooh). It was also nominated for the Academy Award for Best Animated Short.