Piglet decides to display a brown shoe with a daffodil, and one of the most confusing misunderstandings ensues, with Owl telling Tigger, Rabbit, Gopher and Pooh that it is a running trophy. Because they won't let Piglet correct them, they decide to hold a race around the Hundred Acre Wood to try and beat Piglet!
One day, Piglet is polishing a brown shoe with a daffodil inside and deciding to put it next to a baby picture of him. Tigger then comes in and says he never knew he had one of those. Piglet tries to explain, but Rabbit, Gopher, Pooh and Owl then come in and try to guess what it is. Owl then says it is a running trophy, and they believe him, and ask Piglet why he never told them. Piglet says it's nothing, but they don't listen. Tigger then takes him outside and asks him how fast he can run to a tree far in the distance and back. Piglet doesn't do anything, but the friends believe it was so fast they couldn't see it!
Owl says that traditionally races are held once a year to let other people have a chance at winning. Piglet tries to give it away, but Rabbit says that it must be won. They all leave, to train for the race, and Piglet is left confused and worried. While they are training, he tries to tell them once again, but they do not listen. That night, Piglet practices what he is going to say at the race tomorrow, saying that he has never won any trophies, so there is no need to have a race. The race day comes, but before Piglet can say it, Owl interrupts and says "Go", so the race begins! Gopher, Rabbit and Tigger are neck and neck, and Piglet is in last.
Gopher skips climbing up a hill by digging through it so that he can be in first place, and Tigger breaks the bridge, causing Rabbit to fall. Meanwhile, Piglet helps Eeyore find his tail and puts it on his back which caused him to run right away. Tigger is in first place, but falls into one of Gopher's holes, and Piglet saves him. Next, one of Gopher's inflated boots deflate, but he has a spare and keeps racing. Unfortunately, the racers approach the swamp, and Tigger, Rabbit, Gopher and Eeyore are stuck. The racers beg Owl to get them out. But Owl, wanting to keep the race fair, refuses to help them, stating that whoever he helps out of the swamp first would gain an unfair advantage. Piglet witnesses this, and rushes to Pooh for help. Pooh tells him if they can't finish the race, bring the finish of the race to them. Piglet uses the finish line to pull Tigger, Gopher, Rabbit and Eeyore out of the swamp.
Piglet still cannot tell them, so decides to do something unexpected and leave the Hundred Acre Wood. Owl, Tigger, Rabbit, Pooh, Gopher and Eeyore come to tell him he won, as he crossed the finish line first and saved them with it. Piglet is awarded the trophy, and says it'll look very good next to the trophy he won for weight lifting! Everybody stares at Piglet incredulously and he flexes a muscle, and says he's just kidding.