Original air date: 09/27/2009 Runtime: 22:14 min. Everyone’s favorite soft-spoken neighbor, Cleveland Brown, is on the move after he decides it’s time for him and Cleveland Jr. to leave Quahog and go west. On their way to California, the duo makes an pit stop in Cleveland’s hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Although she comes with baggage in the form of a rebellious teenage daughter and a sharp-tongued 5-year-old son, Cleveland is still in love with Donna and is determined to start a new life.
Original air date: 10/04/2009 Runtime: 21:42 min. Cleveland tries to make inroads with Roberta by asking her to accompany him to the school's father/daughter dance. The evening seems to be going smoothly until Cleveland has a mishap with the family pet and kills his chances of being accepted by his new kids.
Original air date: 10/18/2009 Runtime: 21:41 min. 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.
Original air date: 11/08/2009 Runtime: 21:37 min. When Cleveland has "the talk" with Roberta, it scares Cleveland Jr. into taking a vow of chastity, but his sworn celibacy may not be all he had hoped for when he overhears Cleveland making fun of him. Meanwhile, Rallo shows an interest in attending church.
Original air date: 11/22/2009 Runtime: 21:43 min. Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie (guest voice Francis Callier) and Freight Train (guest voice Craig Robinson) as well as Donna’s Auntie Momma (guest voice Kym Whitley) who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline (guest voice Jamie Kennedy) decide to celebrate on their own, and Cleveland discovers a surprising secret about Auntie Momma that changes his impression of her forever.
Original air date: 11/29/2009 Runtime: 21:41 min. 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.
Original air date: 12/13/2009 Runtime: 21:44 min. Celebrate the holidays Stoolbend-style! 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.
Original air date: 01/03/2010 Runtime: 21:43 min. 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.
Original air date: 01/10/2010 Runtime: 21:42 min. Roberta's new teacher, Ms. Eck (guest voice Jane Lynch), encourages Roberta to alter her appearance to teach her an important lesson, and Cleveland Jr. befriends the disguised Roberta only to fall in love with her. Meanwhile, Cleveland and the guys set out to invent the next infomercial product.
Original air date: 01/31/2010 Runtime: 21:42 min. 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.
Original air date: 02/14/2010 Runtime: 21:41 min. 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.
Original air date: 02/21/2010 Runtime: 21:41 min. Cleveland teaches Junior responsibility by challenging him to get a job, and to his own delight, Cleveland Jr. lands a job working at The Stool. However, when Cleveland Jr. starts commenting on the number of beers his father consumes and sets limits on the guys’ time at the bar, a feud erupts between father and son. Meanwhile, Roberta competes with Lacey (guest voice Ashley Tisdale), the rich girl in school, and gets more than she bargained.
Original air date: 03/21/2010 Runtime: 21:26 min. 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.
Original air date: 03/28/2010 Runtime: 21:42 min. 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.
Original air date: 04/11/2010 Runtime: 22:03 min. When Cleveland is diagnosed with high cholesterol, Donna puts him on a new high-fiber diet, which causes him some 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.
Original air date: 05/02/2010 Runtime: 21:42 min. 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 an epic Stoolbend rap battle to compete for Chanel’s heart.
Original air date: 05/09/2010 Runtime: 21:41 min. 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 his confederate flag-owning neighbor.
Original air date: 05/23/2010 Runtime: 21:32 min. Much to his dismay, Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife’s belongings and that his parents, Cookie (guest voice Francis Callier) and Freight Train (guest voice Craig Robinson), plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna’s ex-husband, Robert (guest voice Corey Holcomb). In the end, though, Cleveland steps in to save the day on the Season Finale of The Cleveland Show.