10 Sports Betting Wins You Won’t Believe

Sports Team Walking on Field, Sports Fans in Stands, Money
Every so often I come across a story about a sports gambling win that makes me shake my head with envy. I’m talking about those double-digit wagers that result in thousands of dollars in winnings. Needless to say, these longshot bets rarely prove to be fruitful, but when they do, it’s as exciting (or even more) as the game itself. I’ll list some of the greatest wins I’ve seen and maybe you’ll be inspired to throw down a bet on an unlikely outcome….you know, just in case.

1 – Safety First

Safeties just aren’t all that common in football, and at the time of this bet, there had only been seven total in Super Bowl history. Nevertheless, Jona Rechnitz put up $1,000 dollars for a safety to be the first score in Super Bowl XLVI. The rest is history. He cashed in for a $50,000 win when Tom Brady was flagged for intentional grounding while throwing from his own end zone.

2 – Endurance Pays

Granted, this win wasn’t on a bet you could place at a sportsbook, but it’s also too good to leave off the list. Poker player Erick Lindgren decided to wager with his buddy, notorious gambler Phil Ivey, and others, that he could have a golfing day for the ages.

The bet went like this: Lindgren had to play four rounds in the scorching Las Vegas heat, carry his own bag, walk each hole, and shoot under 100 each round.

After 20 miles walked and 72 holes of golf, Lindgren took home more than $300k.

3 – Betting on the Birds

Winning a bet against all odds is great, but when your team’s success makes you money it’s that much sweeter.

Live St. Louis Cardinals Baseball Game

While they were five games back of a Wild Card spot with just 15 games left, an unnamed St Louis Cardinals fan threw down $250 on the Cardinals making it to the fall classic (500:1 odds). In an apparent attempt to outdo himself, he wagered another $250 on the red birds winning the World Series at 999:1 odds. One amazing playoff run later, he netted $375,000 on his initial $500 investment.

4 – Family Matters

The fact that Rory Mcllroy was ever a huge underdog might come as a surprise, but even he had to start somewhere. There’s nothing like getting support from one’s father, and Mr. Mcllroy put his money where his mouth was.

Gerry Mcllroy, along with a few friends, placed a bet worth USD $257 that a 15-year old Rory would win the British Open within the next 10 years. The odds for the bet were 500:1.

With one year to spare, a 24-year old Rory Mcllroy won the open and his dad’s bet nine years prior paid out nearly $228 in US dollars.

5 – Fail Mary Miracle

Do you think Golden Tate legally scored the touchdown in infamous “Fail Mary” Monday night game in 2012? We know one person who does. Canadian Gino DiFelice threw down just $5 on a 15-leg parlay on the NFL weekend. Little did he know those bets (with the assistance of his young daughter) would result in life-changing money by Tuesday morning. Imagine waiting on the replay officials to get finalize the call with…wait for it…$750,000 on the line. Luckily for our friend north of the border, it all worked out.

6 – Super Prop Parlay

The Super Bowl sees more prop bets than any other sporting event in the world, and one unnamed bettor got in on the action before Super Bowl LII with a modest $15 play as a 9-leg parlay.

Philadelphia Eagles Live Game, Fans Cheering

Although he did correctly choose the Eagles +4.5, more obscure bets such as the number of total 3rd down conversions (Over 11.5 if you were wondering). As the clock hit 0:00 our lucky anonymous Eagles fan raked in $6,000 on his initial $15 bet. We cannot confirm nor deny if he took off work on Monday to celebrate.

7 – Eye of the Tiger

Everyone loves a good comeback story, and the 2019 Masters Tournament provided one we’ll remember for decades to come. For James Adducci, it was a moment he’ll remember every day for the rest of his life.

Adducci wasn’t a seasoned sports bettor, in fact he said the only other bet he’d placed in his life was that Arnold Schwarzenegger would win the 2003 election for governor of California (he was right, too).

After shopping around for a book that would accept his $85,000 cash wager, he finally got ahold of sportsbook William Hill U.S CEO Joe Asher. Asher allowed the bet, and after draining his bank account to place the bet, Adducci was rewarded with a $1.19 million payout.

8 – Pitch Perfect

There are low odds, and then there are 5,000:1 odds. These were the odds that sportsbooks gave the Premier League’s Leicester City to win the title in 2015. Just before the team made their historic and unlikely run, an anonymous gambler placed a 100-pound bet. At the time of the bed the odds had evened out a little bit (2000:1) but it stands to reason that nobody was anticipating what would happen next. Leicester City completed one of the most notable underdog stories in sports, and our anonymous bettor took home more than USD $250k.

9 – Lefty Wins Big

Hearing a story about a really rich guy getting even richer might not be everyone’s cup of tea, but here we are anyway. Phil Mickelson, a major sports gambler, placed a mere $20,000 futures bet on the Baltimore Ravens winning the Super Bowl in 2000. At 22/1 odds, winning was a longshot.

Live Baltimore Ravens NFL Game

As if he needed the money, Lefty ended up taking home $560,000 as Ray Lewis willed the Ravens to a championship. To add to his already absurd winnings, he reportedly bet on the eventual winner of the World Series, the Arizona Diamondbacks, in the same year. Some guys just have all the luck.

10 – No Blues Here

The St. Louis Blues occupied last place well into the 2019 NHL season and winning their first Stanley Cup looked more than unlikely. That didn’t stop Blues fan Scott Berry from supporting his team by way of a $400 bet at 250-1 odds.

Sportsbook Winning Ticket for NHL Stanley Cup

Despite offers from sports books to hedge his bet (one book offered him $75k when the Blues went up 3-2), he stuck with his team and enjoyed a 4-1 win in game 7. For his efforts, he received $100k.


Winning hundreds of thousands of dollars on a low-odds sports bet is something that few gamblers will ever experience during their careers. However, these stories serve as reminders that if you put the money down, you’ve always got a chance to win big. Do your research and find a longshot bet that feels right to you and there might be a spot on the next list talking about your unlikely victory.