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How to Gamble With a Chance of Winning (with Pictures ... If you want to gamble with a chance of winning, choose table games with favorable odds, like Blackjack. Statistically, Blackjack is the game where you are most likely to win some money. You could also fare well by playing Roulette and placing 50/50 bets, by betting on black, red, evens, or odds. Simon’s Guide to Making Money Like A Professional Gambler