Does Anyone Ever Win Sweepstakes? Many people often wonder about the odds of winning these contests. While the chances can be slim, there are indeed real winners who have struck it lucky. Stories of individuals winning cash prizes, vacations, and even cars circulate frequently, fueling the belief that it’s possible. However, it’s essential to approach sweepstakes with realistic expectations. Does Anyone Ever Win Sweepstakes? Yes, but it’s crucial to remember that for every winner, countless others enter without a prize.