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; Cleveland challenges her boyfriend to a rap battle.

Donna puts Cleveland on a new diet; 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 between his wife and his friends.

Cleveland tells Cleveland Jr. to get a job and he does—at the Stool. Meanwhile, Roberta competes with the rich girl at school (voice of Ashley Tisdale). Other guest voices include Kristen Wiig (Mrs. Stapleton), Ed Asner (Editor) and David Lynch (Gus).

Holt admits to Cleveland that he wishes he had a special someone in his life. Cleveland, determined to help his friend, introduces introduces him to a cat-loving redhead who ends up being more than Holt can handle. 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 (voice of Jane Lynch) 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 former NBA star Scottie Pippen have voice cameos as themselves.

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.

After having too much egg nog at the office party, Cleveland spills the beans about Rallo’s father. Cleveland tries to reconnect father and son in an attempt to save Rallo’s Christmas spirit. Meanwhile, Roberta becomes an animal rights activist and tries to save a reindeer.

Cleveland is upset when he finds out that Donna is still attending a single mothers’ support group.

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

Cleveland lands a new job with a little help from Tim the bear. Meanwhile, Rallo and Roberta plan to get Cleveland Jr. in touch with his feelings.

Attempting to get Cleveland Jr more friends, Cleveland invites the neighbor kid over to the house. However, when he overstays his welcome, Cleveland has a rough time trying to get him to leave.

Cleveland, wanting to make his new stepdaughter like him more, asks her to accompany him to the school’s father/daughter dance. All goes well until Cleveland has a mishap with the family pet and ruins his chance.

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