A highlight episode of the last three years.

Kevin is upset to learn that Paul will be attending a prep school when they enter high school next year.

Karen decides to move into a house that needs fixing up, when Jack insists on helping with the repairs they arrive to find that Karen's roommate is her boyfriend.

Kevin sees Winnie for the first time since right after they broke up.

Kevin is recruited to be on the yearbook staff and make up quotes about people. Kevin has second thoughts when he gets to know one of the students.

After Karen announces she won't be coming home for summer break, Kevin and Wayne fight over who should move and who should stay in there room.

Kevin is left embarrassed when his mother takes a job in the office at school.

Kevin and his father are forced together on a road trip to buy a new suit for Kevin.

The family dog, Buster, has been acting strange and a visit to the vet reveals Buster should be fixed.

Kevin puts off going back to the dentist to have a cavity filled because he doesn't want to chicken out in front of the dental hygienist he has a crush on.

Grandpa Arnold arrives in town and convinces the family to attend the funeral of a distance relative.

Kevin convinces Paul to throw a party and invite Winnie in an attempt to get her back.

Kevin is excited when a joint field trip is announced with Winnie's school but things end in heartbreak.

Paul nominated Kevin for student council President pitting him against Becky Slater.

Kevin accidentally discovers that Coach Cutlip is working as Santa Claus at the mall.

One thing has always been a certain, Kevin would beat Paul in basketball. When Paul tries out for the school basketball team, his skills improve leaving Kevin behind.

After expenses mount in the Arnold household, Jack asks for a raise at work which he gets plus a promotion that will interfere with him making it to Thanksgiving dinner.

Kevin reluctantly agrees to escort Paul's little sister to her dance.

Kevin is partnered up with Madeline for a school project but while at her house, Kevin loses his ID bracelet that Winnie gave him.

Looking to make extra money, Kevin takes a job as a caddy at a golf course.

Kevin and his friends attempt to crash a 10th grade girls slumber party.

Kevin has a miserable first day of high school.

The family attends Jack's work picnic and learn Jack was passed over for a promotion.