With the end of the summer approaching, the Arnolds decide to attend Jack's Labor Day work picnic. When it is learned that Jack was passed over for a promotion that goes to one of his rivals, tensions grow high between him and Kevin, who wants to prove that he is no longer a little kid.
On his first day of the ninth grade, Kevin is bullied out of his locker, humiliated by Becky Slater, scheduled for the wrong class, and meets a new girl who diverts his attention away from thinking of Winnie Cooper who is now at a different school.
With his allowance not going as far as he hopes, Kevin takes a job as a caddy at a local golf course. However, Kevin is dismayed when he finds out that he's caddying for his Dad's boss at NORCOM (who just happens to be playing golf against Jack Arnold, Kevin's Dad).
Kevin receives an I.D. bracelet from Winnie Cooper as a present. The next day, Kevin is assigned to work on a French assignment with an attractive girl named Madeline. However, after working on their project at her house, Kevin rushes out in a panic, leaving Winnie's bracelet behind. Now Kevin has to get the bracelet back in time for his date with Winnie the next night. But how?
Money is tight around the Arnold household, and things don't look so good when the kitchen stove finally dies. Jack goes to NORCOM to ask for a raise, and gets it, as well as a promotion. With the new stove in the kitchen, it seems the Arnold's problems are over, until it becomes clear that Jack won't be back for Thanksgiving Dinner.
When Paul decides to try out for the basketball team, Kevin is convinced that he is just wasting his time. However, when he ends up making the team and his basketball skills improve, it creates a strain in their friendship.
While at the mall, Kevin is surprised to find gym coach Cutlip playing the seasonal job of Santa Claus. When Cutlip realizes that Kevin knows, he gives him preferential treatment in gym class in hopes that Kevin won't tell his secret.
With Becky Slater as the only candidate for Student Council President, Paul convinces Kevin to run a campaign against her. With the deadline approaching and way behind, Kevin is tempted to use less-than-honest measures to try and win the election.
Both Kevin Arnold and Winnie Cooper's schools are having a joint field trip to the local museum. Kevin figures this will be a great chance to spend some time together with Winnie, but things don't turn out as he planned.
After getting dumped by Winnie, Kevin begins to doubt whether it is really over between them. In hopes of getting her back, he convinces Paul to throw a party and invite Winnie. However, things don't go as planned when Winnie decides to bring her new beau, Roger.
Following the death of a very distant relative, Grandpa Arnold comes to visit and convinces the family to attend the funeral and burial. While at the event, Kevin begins to think about the mortality of his dad and grandfather.
Following a trip to the dentist, Kevin finds out that he needs to have a cavity filled. He puts off going back in fear that he will look like a coward in front of the lovely dental hygienist, who is always complimenting him on his courage.
Kevin is forced to take a one-hour drive with his dad to get fitted for a new suit. Things don't go as planned when his dad gets them lost and refuses to listen to Kevin, who desperately tries to help.
When his mom takes a job in the attendance office at his school, Kevin worries that his life is "ruined". After his mom embarrasses him during a fire drill, Kevin tells her to no longer talk to him while at school.
Kevin and Wayne are at each other's throats over sharing the same room. When it seems that Karen will no be needing her old room, the two see her moving out as an exciting opportunity. But soon, Wayne and Kevin can't reach an amicable decision over who gets Karen's room, and who stays in the old one.
Kevin is recruited by the yearbook staff to come up with quotes to describe certain people in school. However, Kevin begins to have second thoughts when it seems that one of his descriptions could hurt one student's feelings.
After breaking up two months ago, Kevin sees Winnie for the first time. However, it becomes obvious to him that she has changed and is no longer the same girl that he knew growing up. When he sees that she is now hanging around with 11th graders in cars, he worries that he is nothing more than a piece of her past.
On the eve of his graduation from Junior High, Kevin is excited about entering high school next year with Winnie and Paul. However, those feelings change when Paul announces that he will be attending a prep school next year. He begins to fear that his world will change after graduation.
A highlight montage of the past seasons. Examines Kevin Arnold's relationship with Winnie Cooper in particular and touches on all the main characters and story lines that have been present so far in the season.