After losing the house to Loretta in the divorce and becoming fed up with Peter's shenanigans, Cleveland decides to leave Quahog with Cleveland Jr.

He decides to drive cross country to California pursue his baseball dreams but gets sidetracked in his hometown of Stoolbend, Virginia and by chance runs into his old high school flame Donna.

Cleveland gets acquainted with Donna's kids Rollo and Roberta and Donna's friends, Holt, Lester and Tim (the Bear) as well as her ex-husband Robert.

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.

In the search for a friend for Cleveland Junior, Cleveland accidentally takes in Ernie Krinklesac, Lester's son.

After taking Donna's advice, child services becomes involved and Cleveland and Lester must get his son back.

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 Jr.'s vow of chastity may not be all he had hoped for after he overhears Cleveland making fun of him.

Meanwhile, Rallo takes an interest in attending Church.

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

Cleveland celebrates his first Thanksgiving with his new family and discovers a surprising secret about Donna's Auntie Momma.

When Cleveland Jr. and Roberta go on a school trip, Cleveland and Donna are excited to have the house to themselves. However, Rallo tries his best to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.

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 an animal rights activist and tries to save a reindeer

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.

While Ms. Eck, Roberta's new teacher, encourages her to change her appearance to learn an important lesson, Cleveland Jr. befriends the disguised Roberta only to fall in love with her afterwards.

Meanwhile, Cleveland receives help from the guys in order to invent the perfect infomercial product.

Coach Cleveland comes to the rescue of frustrated parents by taking a group of delinquent teens under his wing. With the help of Cleveland Jr., he creates a new club dubbed "The Crazy Eights", and hopes that it will keep the kids on the straight and narrow. However, he is soon mixed up in bad business, and only the "Crazy Eights" can help him out.

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 Jr. gets a job at the local newspaper, and begins to learn responsibility. When he starts making changes to the bar that Cleveland and his friends hang out, a good old fashioned father-son rivalry breaks out. Meanwhile, Roberta gains a rival, who just happens to be wealthy, so her and Rallo plot a surprise for this new friend.

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.

When Cleveland and Donna are mugged at an ATM, Cleveland is accidentally wounded in the tussle.
By the time the story hits the local news, the attention goes to Cleveland's head, but Cleveland's version isn’t the whole story.

Meanwhile, Roberta takes advantage of Rallo, who thinks that his sister is dying of a terrible disease.

When Cleveland is diagnosed with high cholesterol, Donna puts him on a new high-fiber diet, which causes an intestinal backlash. It may stink up the place, but Cleveland quickly realizes his gas might score him a few points in the Broken Stool's karaoke contest.

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

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.

After Cleveland gambles away Roberta's college fund, Kendra discovers that Cleveland was actually cheated out of his money and recruits Donna and Arianna for a mission.

Much to his dismay, Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife's belongings and that his parents, Cookie and Freight Train, plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert. In the end, though, Cleveland steps in to save the day.