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  • Created On:
    09/07/2011 9:56 PM
  • Last Update:
    06/08/2017 10:19 AM

BIGGEST Gambling Wins in History

Here are the details of some of the biggest wins by players over the house:

Event: Super Bowl 20 (1986)
Prop bet: Would William The Refrigerator Perry score a touchdown?
Odds: Opened at 20-1 . . . closed all the way down to 2-1
Result: He scored a TD in the 3rd quarter.
Vegas loss: Some estimate upwards of a half-million dollars on this bet alone.
Note: THE prop bet that spawned the prop betting frenzy every after.

Event: Super Bowl 42 (2008)
Action: Overall Super Bowl betting
Vegas loss: over 2.5 million dollars
Note: Worse loss since figures began being tracking in 1991

Event: 1998 NBA Champs
Winner: Chicago Bulls
Bulls going for three straight titles; 6 in 8 years.
Future Odds: Amazingly, the Bulls in some sports were small favorites to win the title vs. the entire league (the odds were better on the Bulls, than all other teams combined) . . . that didn't stop the public from betting the Bulls huge - giving the books huge exposure, and ultimately, a huge loss.

Event: 1996 World Series Champs
Winner: NY Yankees
The Yankees had not the World Series since 1978, but every year the Yankee nation would bet big future money of them winning it all. But as the years of failure went by, the odds drifted upwards - till finally some sportsbooks were offering 10-1 on the Yanks winning it - which they did in 1996, giving the players a big payout.

Event: Super Bowl 13 (1979)
Pittsburgh opened -2.5 . . . went up to -5 . . . then closed at -4 . . . Steelers won 35-31 . . . so, the early Pittsburgh money (which moved the line up) won as did the later Dallas money (which moved the line down) . . . and the final money at -4 pushed (which is like a tie, meaning the bettors get their money back).
Vegas loss: an estimated 35% of total money bet was lost by the sportsbooks. Sportsbooks typically win about 4% of money bet.
Note: called Black Sunday

Event: Super Bowl 23 (1989)
Bob Stupak,
the legendary gambler and casino owner from Vegas, risked a cool $1 million on Cincinnati, plus 7 against San Francisco. The 49ers won, but did not cover the spread giving Stupak the biggest recorded Super Bowl payday.

Event: Buster Douglas vs. Mike Tyson
Date: 2/11/90
Odds: Tyson a 42-1 favorite over Douglas.
Result: Douglas won by knockout thus creating one of the biggest underdog payouts in sports betting history.

  • Straight from Vegas ...

RJ Bell is the founder of – a two-time INC. 5000 company, as well as the largest American digital media organization covering Las Vegas news and odds. Pregame is the exclusive odds provider... Read more

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