Does anyone actually win sweepstakes? Many people often wonder about the odds of winning these contests, as they seem too good to be true. While it's true that millions enter sweepstakes, there are real winners who walk away with prizes ranging from cash to luxury vacations. However, the chances of winning can be slim, depending on the number of participants and the prize pool. Ultimately, while skepticism is common, the answer to "Does anyone actually win sweepstakes?" is a resounding yes—just not everyone who enters will be lucky enough to claim a prize.