These Are Some Of The All-Time Jaw Dropping Wins In Sports Betting History Throughout the long and storied history of sports betting, there are countless examples of incredible wins that brought the gambler in question a massive return on the money that they laid down. The list of biggest wins in the history of sports betting is nearly endless and there is not enough room to present a comprehensive list. With that in mind, there are 3 of the most noteworthy and famous sport betting wins that have been achieved in the last few decades. These are examples of gamblers who scored major wins by defying the odds on teams and athletes that were considered to be long shots. The first big win to make this list was achieved off of the sport of baseball as where the final two are notable wins that sports betters have achieved by gambling on the NFL. Cashing In On Kansas City Dave Oancea is a bit of a legend in the world of sports betting. This is so much the case that he is fondly referred to as Vegas Dave. He has had many legendary wins throughout his sports betting career, but among these, perhaps the most notable was his 2015 World Series win when he made the call to take the Kansas City Royals at 30/1. Vegas Dave risked $140 thousand and he had to spread the money out at fifteen casinos, but when this gambling game through at the end of the season, he cashed in on a monumental $2.5 million. A Basketball Legend Wins Big On Another Sport Charles Barkley is undoubtedly the most celebrity status laden member of this list of sports betting winners. He is famous for his exploits on the basketball courts of the NBA during his long and storied career and he also has a reputation for being an avid sports betting enthusiast. Though famous for his work on the basketball court, one of the biggest wins in the life of Charles Barkley came when he accurately predicted that the New England Patriots would defeat the St. Louis Rams in the Super Bowl. Charles took the risky stance of betting on the underdog in this game, but the result was a massive win of $800 thousand. Talk About Return On Investment The final installment on this list is an example of truly cashing in and turning a small bet into a massive payday. This was exactly what Tayla Polia did when she placed a $5 sbobet on a 2015 NFL season parlay. She ended up hitting on all the of different selections within the scope of her parlay and this transformed her tiny $5 bet into a massive score of $100 thousand. Talk about return on investment.