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.
On his first day of high school, Kevin quickly realizes that it is not quite the same as junior high where he knew everyone and was the high man on the totem pole. He is followed by an annoying classmate, bullied by Wayne, and picked on by an egotistical teacher.
Denise and Frank seem to be made for each other, until Denise turns her eye to Kevin because he understands poetry. Although she breaks up with Frank and kisses Kevin, Kev thinks it would be better if she went back to Frank because they are a perfect match.
After being cut from the football team, Kevin finds out that McKinley High has a soccer team. He signs up for the team but soon realizes that most of the kids on the team are nerdy and un-athletic and the coach is a legendary former football coach whose best days have passed him by.
For Jack's 43rd birthday, Norma decides to try and repair his relationship with Karen by having them meet at a restaurant. Her plan begins to backfire when Jack continues to begrudge Karen's live-in boyfriend Michael.
Alvin Pfeiffer's investment in some oceanfront property pays off. But while the both the Arnold's and the Pfeiffer's seem happy over the new developments, Jack Arnold seems a bit put-off by Alvin's new spending habits.