The beauty of sports is that you never quite know what will happen in any given day.
Never in my wildest dreams did I think I’d be writing up an article on World No. 1 Jannik Sinner losing in the second round at Roland Garros to unranked Juan Manuel Cerundolo, but here we are.
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Sinner was the -300 favorite to win the entire tournament and had pre-match odds of -50000 at DraftKings ($500 wager would win $1), with Cerundolo as a massive 32-1 underdog. At one point in the third set, Sinner was up two sets to none and up 5-1 in the third set, and had odds as long as 100-1 at various sportsbooks.
One bettor wagered $50,000 on Sinner at 98% on the prediction market Kalshi, which would have won $949.07, but instead he went home with nothing.
Just how big an upset was this according to the odds?
Here is how it compares to a few other recent single-game upsets across sports, ranked by pre-match odds:
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85-1 odds
2019: Stephen F. Austin over Duke, college basketball
The Duke Blue Devils entered this Nov. 26 game at Cameron Indoor Arena as 28.5-point favorites and they hadn’t lost a non-conference game there under Coach K in 150 attempts. Stephen F. Austin was a stunning 85-1 on the moneyline before the game, and won 85-83 on a walkoff layup at the buzzer. An upset for the ages.
80-1 odds
2022: Eastern Illinois over Iowa, college basketball
Eastern Illinois entered the Dec. 21 game against Iowa ranked 356th in KenPom and as a 31.5-point underdog. The Panthers were 80-1 underdogs on the moneyline at some sportsbooks before the game. Underdogs of at least 30 points in college basketball had been 0-558 over the past 30 seasons entering that game, according to ESPN Research.
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2022: Rich Strike wins the 148th Kentucky Derby
A late replacement for Ethereal Road, Rich Strike won the Kentucky Derby as an 80-1 long shot, outlasting Epicenter and Zandon to cash with the longest odds for any Derby winner since 2000.
42-1 odds
1990: Buster Douglas over Mike Tyson, boxing
In the biggest upset in modern history, Mirage sportsbook director and Las Vegas legend Jimmy Vaccaro hung 27-1 for Douglas’ odds, which were quickly bet up to 42-1. Douglas knocked Tyson out in the 10th round.
32-1 odds
2026: Juan Manuel Cerundolo over Janik Sinner, tennis
The unranked Cerundolo was down two sets to Sinner, but ended up winning 19 of the final 21 games to shock the top-ranked player in the world. Sinner was a -300 favorite to win the French Open heading into the tournament.
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25-1 odds
2022: Saudia Arabia beats Argentina in World Cup, soccer
In one of the biggest upsets in World Cup history, Saudia Arabia beat Lionel Messi’s Argentina team 2-1, after falling behind 1-0 in the first half. Saudia Arabia scored goals in the 48th and 53rd minute to take the lead and hold on for the stunning result. Argentina would go on to win the World Cup.
2018: No. 16 UMBC defeats No. 1 Virginia in NCAA tournament, college basketball
The first No. 16 seed ever to defeat a No. 1 seed in March Madness, UMBC dominated Virginia as a 20.5-point underdog and the second half wasn’t even close. UMBC ended up winning 74-54
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Honorable mention
2017: Howard beats UNLV, college football
Led by Cam Newton’s younger brother Caylin, the FCS Bison shocked UNLV 43-40 as 45-point road underdogs on Sept. 2, 2017. It’s the biggest upset by the point spread in college football history, per ESPN Research. Las Vegas sportsbooks didn’t offer a moneyline on the game, but ESPN’s David Purdum reported that offshore books had the Bison as 600-1 underdogs on the ML before the game.

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