While having fun at the Sea Fair, the Cup Brothers run into Ms. Chalice, who seeks their help to help an old acquaintance of hers. This person is on a treasure hunt for the Treasure of Blue Belle Island. But the Cup Trio and their alley adventured through the island; the Devil tried to sneak away from King Dice and Henchman to go after Cuphead's Soul again.

The Cup Trio were about to watch the Inkwell Races until the Devil showed up for Cuphead's soul again. However, this made him and Cuphead end up hit by a truck, taken to the hospital, and bedridden due to their broken right legs as they share a room with a lion angel who holds a grudge against the Devil as Mugman and Chalice try to get to Cuphead.

What was supposed to be a relaxing shopping day at the Farmer's Market turned into another troubling adventure when Cuphead's head got taken by a flying bird and landed in the area of Baroness Von Bon Bon, a "sweet" lady with a head collection. With Mugman and Ms. Chalice helping his headless body, they go on a quest to save Cuphead's head and avoid getting their heads removed too.