What are the chances of winning a Microsoft Rewards Sweepstakes? The odds can vary significantly based on the number of entries and the specific sweepstakes rules. Generally, the more entries you accumulate through activities like searching with Bing or completing quizzes, the better your chances become. However, since many participants are vying for the same prizes, it’s essential to understand that while your efforts can improve your odds, winning is never guaranteed. Ultimately, what are the chances of winning a Microsoft Rewards Sweepstakes? It’s a mix of strategy, persistence, and a bit of luck.