Cleveland Brown and Cleveland Jr. leave Quahog and take to the road. On their way to California, they stop in Cleveland's hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Cleveland, still in love with Donna, is determined to start a new life with her, even if Donna's kids aren't exactly angels.

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.

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.

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.

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

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 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.

After a nostalgic flashback to the glory days as his high school's baseball all-star, Cleveland visits his Alma Mater to find out there's no longer a team.

Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. Cleveland then steps in as head coach and dusts off his retired jersey in an attempt to convince Cleveland Jr. to play ball instead of joining the math club

In order to teach her an important lesson, Roberta's new teacher encourages her to alter her appearance. Unbeknownst to him, Cleveland Jr. befriends, and falls in love wit the disguised Roberta.

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 (guest voice Fergie), 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.

Roberta and Rallo have a surprise for Lacey, Roberta’s wealthy rival. Meanwhile, Cleveland Junior learns responsibility while working at The Stool, but when he starts making changes to the guys’ hangout, a feud erupts between father and son.

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 was a hero. Meanwhile, Roberta convinces Rallo that she might be dying of a terrible disease and makes him do her bidding.

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. Meanwhile, Quagmire pays a visit to Stoolbend to deliver Cleveland some upsetting news.

Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams; Cleveland Jr. 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 "Cleveland's Angels" mission.

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.