- In the first two seasons, any family who won the game by finding the Top Cash Card. The total on the Monopoly Crazy Cash Machine would keep going... and going... until that Top Cash amount was hit.
- Later on, anyone who opened the Community Chest, picked a Cash Card on the first three levels that had money on it, and picked the "WIN" Card on the final level.
- One family lost their main game (Sorry!) but went on to open the Chest and go all the way to win the car in their episode.
- One family won the Barrel of Monkeys game on the fourth pick.
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