Do people actually win sweepstakes? Yes, many individuals do win various contests and sweepstakes every year, often sharing their success stories online. While the odds can be slim, especially for large-scale promotions, countless smaller sweepstakes offer better chances for participants. Do people actually win sweepstakes? Absolutely, but it's essential to approach them with realistic expectations and to be cautious of scams. Engaging in legitimate contests can lead to exciting rewards, making the experience worthwhile for those who enjoy the thrill of the game.