The Dalmatians are in a "Bark Brigade" running course. Tripod comes in first and Lucky in second. Lt. Pug tells all the pups that they will not qualify as cadets until they beat the "Obstacle Course of Unspeakable Pain and Agony."
Lucky is determined to beat Tripod and be top dog of the cadet corps.
The course begins with the pups needing to jump through tires, Lucky and Tripod do this with ease whilst Cadpig (not big enough to even reach the tires) finds an alternative and just runs underneath. Spot is able to fly up to the tires; however, Rolly's jump to her, causes her to shoot into a tree. Rolly begins swinging out of control on one of the tires before eventually rolling into Spot.
The Dalmatians then cross a road; however, Spot is hesitant since she can't cross the road without a reason why. Lt. Pug, however, kicks her across anyway.
Lucky is soon able to get ahead of Tripod; however, he gets stuck in a log bridge, giving Tripod the lead once again. When Cadpig, Rolly and Spot cross the bridge, Rolly sees a persimmon on the other side and jumps over Cadpig and Spot to get to them. The log begins to roll out of control resulting in Spot being shot up into the sky, Cadpig to land in the mud while Rolly gets the persimmons when he collides with the tree, to which Cadpig hits the tree again and buries Rolly in a pile of them.
Lucky is able to overtake Tripod again in the swimming section in Hiccup Hole and the two begin racing up a rock climb. Meanwhile, with Cadpig and Rolly, Cadpig wonders where Spot went before the chicken lands with force on the bank of the water.
As the three begin to climb the rock face, rocks begin to fall. Rolly uses Spot as a shield; however, a small rock hits him on the head and he begins falling with Spot. They are then saved when Spot grabs a loose branch.
Rolly calls for help and Lucky, hearing this, decides to abandon his race with Tripod to go back and help Rolly. He and Cadpig are able to get Rolly and Spot back up with a winch mechanism, using the trees and vines, and the four finish together in last place.
That night around the camp fire, Lt. Pug congratulates Tripod for being Top Dog, Cadpig informs Pug on some tribes who give out gold trophies to those who finish in last place as a salute to their determination, however Pug doesn’t buy it.
Lt. Pug then starts issuing out orders to all the other pups to drop and give him some push-ups; however, the Colonel arrives and orders Pug to hit the deck himself.
Colonel tells Lucky that Tripod informed him of Lucky's sacrifice and finds that very commendable and showing of character. While Lucky is disappointed he can't be top dog or have a rematch, the Colonel comforts him by saying that the course only required him to finish it, and the Colonel adds that he got a sense of pride out of it: a medal that will never tarnish.