While Ms. Eck, Roberta’s new teacher, encourages her to change her appearance to learn an important lesson, Cleveland Jr. befriends the disguised Roberta only to fall in love with her afterwards. Meanwhile, Cleveland receives help from the guys in order to invent the perfect infomercial product.
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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.