When Cleveland needs a new job, Tim hooks him up at Waterman Cable. However, when Cleveland becomes the top salesman, Tim is green with envy and wishes for bad things to happen to Cleveland.

But when Cleveland comes up on some bad luck and misfortune, Tim has a change of heart.

After Cleveland has "the talk" with Roberta, Cleveland Jr. becomes scared and takes a vow of chastity. Meanwhile, Rallo becomes a church greeter.

When Cleveland fills in as Santa Claus at his office holiday party, he has one too many eggnogs and lets the truth slip about Rallo’s father.

After a nostalgic flashback to the glory days as his high school's baseball all-star, Cleveland visits his Alma Mater to find out there's no longer a team.

Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. Cleveland then steps in as head coach and dusts off his retired jersey in an attempt to convince Cleveland Jr. to play ball instead of joining the math club

Coach Cleveland gets greedy to win the high school baseball state championship game and turns to cheating when his star pitcher goes out for the season.

Cleveland and Donna celebrate Valentine’s Day with a trip to Los Angeles after scoring courtside seats to the all-star basketball game. Caught up in the excitement, Cleveland gets rowdy and talks smack to the players from the sideline throughout the game. The basketball champs, feeling hurt, seek revenge by paying a surprise visit to Stoolbend and putting Cleveland in his place.