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.
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.
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.
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.
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
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.
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.
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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