On his first day at school, T-Bone worries that he won't be able to keep up with the rest of the class. The library sponsors an essay contest for "Islander of the Year."
There is a new dog in town and he has only three legs. Clifford, Cleo and T-Bone really like K.C., but they feel uncomfortable and unsure of how to act around him. Clifford's talent for digging seems to be disruptive to everyone in town.
T-Bone finds himself in a contest with Mac. He doesn't win, but he learns that you don't have to win to feel good. The dogs convince themselves that it's okay to keep eating treats as long as they've done something deserve them.
Clifford and Cleo misunderstand a conversation they overhear, and think T-Bone is moving away. When two cats "move in" to the tree next door to T-Bone, the dogs try everything to get rid of them.
All of the dogs are so excited that their old friend K.C. is back on the island for a couple of days-- especially Cleo! Mac is particularly disappointed when rainy weather threatens to ruin his annual Back-to-School Barbecue.