If you land on a square with a blue-haired bombshell on it, or on one of the glowing lavender hearts, you will fight the garishly glam Cherry. Unfortunately, if you defeat her, her face will appear on the Roulette wheel you spin. If you land on her image there and lose the match to her, she will send you to her house on the other side of the board.
Ultimately, you choose your own destiny. When you select the Fastest Bout, you have to defeat each of four challengers in under 90 seconds. If you choose the Survival Bout, you have defeat 20 opponents in a row. In Rodeo, you have to keep th cow at bay for 30 seconds. Rodeo is the easiest, Survival is the hardest and, logically, results in a greater reward.