There have been numerous large bets on the Super Bowl over the years. These are just a few notable examples, but you can expect wealthy bettors to place seven-figure bets on the big game every season. $1 million - Super Bowl XXIII (1989) – Bob Stupak wagered $1 million on the underdog Cincinnati Bengals at +7 against the San Francisco 49ers. The Niners won 20-16, and Stupak walked away with a cool $100,000 or so in profit. $2 million - Super Bowl XLIV (2010) – Phil Ivey put $2 million on Peyton Manning and the Indianapolis Colts to defeat the New Orleans Saints. Of course, the Saints won easily, and Ivey lost the entire bet. $3.8 million - Super Bowl LIII (2019) – Bettor X placed $3.8 million across three separate bets on the Rams to beat the Patriots straight up. Had the Rams won, Bettor X would have earned upwards of $10 million. The Rams lost. To date, this is the single largest bet – and loss – in Super Bowl betting history.