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

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.

Cleveland takes a struggling rapper (Kanye West) under his wing and, together, they write and record a new hit single.