In 1943, the longest recorded streak of one color in U.S. history happened when a player won with the color red 32 times in a row. This is one of the most impressive feats in gambling history.Roulette is infamous for its long odds. In fact, players have a straight-up 37 to 1 chance of winning by betting on one number. This makes it difficult to even win twice in a row. The U.S. record for consecutive wins with one color happened 77 years ago. This speaks volumes of how hard it is to win in roulette.