Cleveland tells his friends that he has lost ownership of his house to his ex-wife Loretta and gained custody of their son, Cleveland Jr., and begins to worry about his future. After Peter (once again) destroys the front of Cleveland's house while he's in the tub, Cleveland decides he has finally had enough of everyone around him hogging all the attention and shenanigans, so he moves out of Quahog with Junior to California to pursue his life-long dream of becoming a professional minor league baseball scout.

Cleveland is excited to have a new family, but his step-kids don't warm up to him. Meanwhile, after being seen kissing his dad goodbye on the cheek, Cleveland Jr. is harassed by everyone at school.

Cleveland, concerned that Cleveland Jr has no friends, invites his neighbor Lester's son Ernie to their house. Ernie becomes attached to the family and Cleveland calls child services to have Ernie taken back home. When the plan backfires, Cleveland helps Lester get his son back.

Tim the Bear helps Cleveland get a new job, while Rallo and Roberta have a plan to help their new brother Cleveland Jr. get in touch with his feelings.

Cleveland and Roberta have "the talk" and scare Cleveland Jr. into taking a vow of chastity. Rallo becomes the greeter at church.

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

Cleveland celebrates Thanksgiving with his new family, with his parents coming over. However, his mother Cookie disapproves of Donna for not falling for Cleveland in the first place and his father LeVar "Freight Train" Brown downright hates his son and had left his mother twice for a waitress.

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.

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.

After Cleveland has a flashback of his days as the high school's baseball all-star, he visits the high school only to find out that there is no longer a team. Principal Wally gives Cleveland a week to raise enough money to re-build the stadium before the baseball season begins. Cleveland becomes the head coach in an attempt to convince Cleveland Jr. to play baseball instead of joining the math club.

Ms. Eck, Roberta's new teacher, encourages Roberta to alter her appearance to teach her a lesson, and Cleveland, Jr. befriends and falls in love with the disguised Roberta. Meanwhile, Cleveland and the guys set out to invent the next infomercial product.

Coach Cleveland rescues a group of delinquent teens. With the help of Cleveland Jr., "The Crazy Eights," and hopes that it will keep the kids out of trouble. He is soon mixed up in bad business, and only the kids can help him.

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 the cat-loving redhead Jill (guest voice Stacy Ferguson). Meanwhile, Cleveland Jr and Rallo anticipate the "birth" of Rallo's pet fish.

Cleveland Jr. is in need of a job, and after failed interviews with a slaughterhouse and a obsolescent newspaper company, it is revealed he is proficient with cleaning up after the customers in the local bar, The Stool.

Cleveland and Donna go on an overdue honeymoon to New York City, however, Cleveland suggests bringing his friends from the Stool, much to Donna's chagrin, to help Coach McFall reunite with a woman from his past. Meanwhile, Roberta, Junior and Rallo stowaway on the trip.

Cleveland and Donna get mugged at an ATM and Cleveland gets shot, and the media makes it seem as if he were a hero. Meanwhile, Roberta convinces Rallo that she might be dying of a terrible disease and makes him do her bidding.

Tim, Arianna, Lester, Kendra, Donna and Cleveland participate in a Karaoke contest at the Broken Stool. However, Cleveland's gas problems, from his new high-fiber diet, end up humiliating Donna. On the meantime, Cleveland and Donna prepare to give some bad news to Cleveland Jr. about Loretta.

Acting as his brother's wingman, Rallo gives Cleveland Jr. a few pointers on how to win over the girl of his dreams, Chanel (guest voice Taraji P. Henson). Although when Cleveland Jr. finds out her boyfriend is local rap star Kenny West (guest voice Kanye West), he challenges Kenny to a rap battle to win Chanel's heart.

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, but the feud subsequently ends when Rallo saves Lester's wife's life.

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 "Cleveland's Angels" mission.

Big news arises in Stoolbend when Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife Loretta's belongings and that his parents, Cookie and Freight Train, plan to remarry