The series features the adventures of Peter Griffins neighbor Cleveland Brown. Many years ago, Cleveland made a promise to his old high school sweetheart, Donna. Cleveland, along with Cleveland Junior, move to Stoolbend, VA to start a new life with Donna and her two children.
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."
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.
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.
When Roberta's new teacher, Ms. Eck, encourages Roberta to alter her appearance, Cleveland Jr. befriends the disguised Roberta and falls in love with her.
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.
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.
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.
Cleveland celebrates his first Thanksgiving with his new family and discovers a surprising secret about Donna's Auntie Momma.
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.
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