Cleveland discovers that his parents plan to remarry and that his father wants Donna’s ex-husband to be the best man.

When Cleveland gambles away Roberta’s college fund, Kendra discovers that he was cheated out of the money.

Cleveland and Cleveland Jr. teach Donna and the kids their tradition of celebrating Black History Month. However, when Rallo learns about his heritage at school, he provokes Cleveland into a battle royale with neighbor, Lester.

Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams and Cleveland challenges her boyfriend to a rap battle.

Donna puts Cleveland on a new diet and Quagmire visits Stoolbend to deliver some upsetting news.

Cleveland is wounded when he and Donna are mugged at an ATM; Roberta takes advantage of Rallo when he thinks she is dying of an illness.

Cleveland and Donna road trip to the Big Apple for an overdue honeymoon, and to Donna’s dismay, Cleveland allows the Stoolbend gang to tag along to help Coach McFall rekindle a long lost romance. Although, when Tim finds himself in a compromising situation and Lester’s language gets him into trouble, Cleveland is forced to choose [...]

Cleveland tells Cleveland Jr. to get a job and he does—at the Stool. Meanwhile, Roberta competes with the rich girl at school.

Holt admits to Cleveland that he wishes he had a special someone in his life. Determined to help his lonely friend, Cleveland introduces Holt to Jill, a cat-loving redhead who ends up being more than a handful. Meanwhile, Cleveland Jr. and Rallo anticipate the “birth” of Rallo’s pet fish.

Cleveland takes a group of delinquent teens under his wing, to the thanks of their frustrated parents. He and Cleveland Jr. create a new club to try and keep the kids on the straight and narrow. However, things don’t turn out so well.

A substitute teacher annoyed by Roberta’s flirty arrogance gives her a fat suit and challenges her to wear it. And Cleveland Jr., who makes a rocket for the science fair, is helped by a new overweight girl in school. Meanwhile, Cleveland, Tim, Holt, Lester and Terry try to invent something. Margaret Cho, Chuck Woolery and [...]

Celebrate the holidays Stoolbend-style! 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. With Rallo’s admiration for his dad destroyed, Cleveland tries to reconnect father and son in an attempt to save Rallo’s Christmas spirit. Meanwhile, Roberta becomes [...]

Cleveland and Donna are excited to have the house to themselves when Cleveland Jr. and Roberta go on a school trip to Washington, D.C., but a disgruntled Rallo will do whatever it takes to keep Cleveland and Donna apart. Meanwhile Roberta’s partying gets out of control and Cleveland Jr. comes to her rescue.

Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie and Freight Train as well as Donna’s Auntie Momma who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline decide to celebrate on their own, and Cleveland discovers a surprising [...]

Cleveland is upset when he finds out that Donna is still attending a single mothers’ support group in order to have a good time. Meanwhile, Cleveland Jr. runs for student council president with Rallo as his adviser.

When Cleveland has “the talk” with Roberta, it scares Cleveland Jr. into taking a vow of chastity, but his sworn celibacy may not be all he had hoped for when he overhears Cleveland making fun of him. Meanwhile, Rallo shows an interest in attending church.

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.

Cleveland is concerned that Cleveland Jr. has no friends, so he invites his neighbor Lester’s son Ernie to their house. A neglected Ernie becomes too attached to the family, leaving Cleveland to call child services to have Ernie taken back home. When the plan backfires, Cleveland helps Lester get his son back.

Cleveland tries to make inroads with his new stepdaughter Roberta by asking her to accompany him to the school’s father/daughter dance. The evening seems to be going smoothly until Cleveland has a mishap with the family pet and kills his chances of being accepted by his new kids.

Cleveland decides it’s time for him and Cleveland Jr. to leave Quahog; Cleveland reunites with an old high school crush, Donna Tubbs.

Cleveland visits his old high school to find out there’s no longer a baseball team team. Given one week, Cleveland attempts to raise money to re-build the stadium before the season begins. In an effort to get Cleveland Jr. to play baseball instead of joining the math club, Cleveland becomes head coach of the team.