Few feelings in sports betting compare to cashing a ticket nobody else believed would win.
A modest favorite winning by a field goal or a run is satisfying, sure, but it's the long shots, the teams and fighters given almost no chance at all, that bettors remember for decades. A +200 underdog carries a real shot at winning; a +5000 or +50000 underdog is a different animal entirely, the kind of bet that turns a few dollars into a life-changing number if it somehow comes through.
Sportsbooks don't set those numbers arbitrarily. A team or fighter sits at +50000 because the outcome genuinely is that unlikely. So when it happens anyway, it sticks. These are the games and fights people still bring up years later, whether they had a dollar on it or not.
Below, we count down some of the most memorable upsets in sports betting history, along with the closing odds and implied win probability behind each one. A few of these payouts are almost hard to believe.
Biggest upsets in sports betting history
| Year | Upset | Odds | Probability |
|---|---|---|---|
| 2015-16 | Leicester City win Premier League | +500000 | 0.02% |
| 1999 | St. Louis Rams win Super Bowl | +30000 | 0.33% |
| 2011 | St. Louis Cardinals win World Series | +20000 | 0.5% |
| 2004 | Greece wins Euro 2004 | +15000 | 0.66% |
| 2004 | Boston Red Sox win World Series | +12000 | 0.83% |
| 2007 | Appalachian State beats No. 5 Michigan | +8500 | 1.16% |
| 2022 | Rich Strike wins the Kentucky Derby | +8000 | 1.23% |
| 1990 | Buster Douglas knocks out Mike Tyson | +4200 | 2.33% |
| 2011-12 | Los Angeles Kings win Stanley Cup | +2800 | 3.45% |
| 2018 | No. 16 UMBC beats No. 1 Virginia | +2000 | 4.76% |
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Notable sports betting upsets
Leicester City win Premier League
We have to start with the biggest upset in sports betting history: Leicester City winning the Premier League in the 2015-16 season. Chelsea opened the year as +160 favorites, with Leicester sitting 13th on the oddsboard at +500000.
A simple $2 futures ticket would have paid out $10,000. The Foxes had finished the previous season 14th, narrowly avoiding relegation after a rough campaign that got manager Nigel Pearson fired. Former Chelsea boss Claudio Ranieri took over, Jamie Vardy caught fire with 13 goals across 11 straight matches, and by Christmas, Leicester sat atop the table, one year removed from the relegation zone.
Books were slow to react. The Foxes were still +1750 on January 1. They kept winning anyway, eventually clinching their first-ever UEFA Champions League berth along the way, and on May 2, 2016, they completed the improbable, cashing preseason tickets at 5000:1.
St. Louis Rams win Super Bowl XXXIV
Expectations were about as low as they get for the 1999 Rams. Sportsbooks set their win total at 5.5 games, ahead of only three teams in the league, coming off a 4-12 season and a roster with a single Pro Bowler on it.
Then the projected starting quarterback, Trent Green, tore his ACL in the preseason, handing the job to an undrafted backup who'd spent three years in the Arena League and one in NFL Europe: Kurt Warner. He threw for 4,353 yards and 41 touchdowns, won league MVP, and led St. Louis to a 13-3 season. By Conference Championship weekend, the Rams were -250 favorites to win it all, a stunning reversal from where the season began. They beat Tennessee 23-16 in Super Bowl 34.
St. Louis Cardinals win 2011 World Series
In late August, the Cardinals trailed Atlanta by 10.5 games in the wild-card race. Their playoff odds bottomed out at 7.7% with 16 games to go, and their World Series odds sat at +20000.
St. Louis won 18 of its final 26 games, completing the largest late-season comeback to make the playoffs in MLB history. From there, David Freese authored one of the sport's iconic moments, a two-strike, two-out triple to force extras in Game 6 of the World Series, followed by a walk-off homer in the 11th to force Game 7. The Cardinals finished the job the next night, beating Texas 6-2.
Greece wins Euro 2004
Greece hadn't reached a major tournament since 1980 and opened Euro 2004 at 150/1, the second-longest odds in the field. Managed by German coach Otto Rehhagel and built entirely around defensive discipline, they beat host nation Portugal in the tournament opener, then somehow kept winning.
Wins over reigning champion France in the quarterfinals and the Czech Republic in the semis set up a rematch with Portugal in the final. Angelos Charisteas scored the only goal of the match in the 57th minute, and Greece became European champions for the first time in program history, a run so unlikely that oddsmakers profited enormously off the tournament as a whole even while paying out a handful of massive longshot tickets.
Boston Red Sox win 2004 World Series
Before 2004, the Red Sox carried an 86-year title drought dating back to trading Babe Ruth to the Yankees, while New York collected 26 championships over that same span. Boston won 98 games in 2004 and took 11 of 19 head-to-head matchups against the Yankees, but when the two met in the ALCS, New York jumped out to a 3-0 series lead. No team in MLB history had ever come back from that hole. Boston's World Series odds sat at +12000.
The Red Sox stole Game 5 in a 14-inning marathon, got a gutsy start from Curt Schilling pitching through a torn tendon sheath in Game 6, and blew out New York 10-3 in Game 7 to complete the comeback. They swept St. Louis in the World Series to end the curse, still the only team in MLB history to erase a 3-0 series deficit.
Appalachian State beats No. 5 Michigan in NCAAF shocker
Michigan opened as a 33-point favorite at home against an FCS opponent, a spread that translates to roughly +8500 on the moneyline. Appalachian State led 28-17 at the half behind four total touchdowns from quarterback Armanti Edwards, then survived a Michigan rally in the fourth quarter, blocking a game-tying field goal attempt as time expired to seal a 34-32 win.
It remains the first time an FCS team ever beat a ranked FBS opponent, and one of the most replayed clips in college football history.
Rich Strike wins 2022 Kentucky Derby
Rich Strike wasn't even entered in the Kentucky Derby until the day before the race, getting a starting gate berth only when another horse scratched Friday morning. He went off at 80-1, the longest price in a 20-horse field, and had exactly one career win to his name heading into the biggest race of his life.
Breaking from the far outside post, Rich Strike sat near the back of the pack through the far turn before surging up the rail in the stretch, running down favorites Epicenter and Zandon to win by three-quarters of a length. It's the second-biggest upset in the Derby's 148-year history, trailing only Donerail's 91-1 win in 1913, and paid $163.60 on a $2 win ticket.
Buster Douglas knocks out Mike Tyson
On paper, this fight wasn't close. Tyson entered at 23 years old with a 37-0 record, 33 of those wins by knockout, and all three heavyweight title belts to his name. Douglas carried a 29-4-1 record and had been knocked out the last time he fought for a title.
What the odds didn't capture was the chaos surrounding Tyson outside the ring: a split from his manager and trainer, a divorce, and a contract dispute with Don King. Douglas, meanwhile, was fighting three weeks after losing his mother. Backed by a 12-inch reach advantage and a relentless jab all fight, Douglas dropped Tyson for the first time in his career with a flurry of punches in the 10th round. Ten seconds later, the belts changed hands.
Los Angeles Kings win 2012 Stanley Cup
The Kings fired head coach Terry Murray in December and brought in Darryl Sutter, who'd led his previous teams to the playoffs in 10 of 11 seasons. LA still limped into the season's final month sitting 10th in the West at +2800 to win the Cup.
A 12-4-3 stretch run secured the eighth and final playoff spot, and from there the Kings' defense locked in, holding opponents to two goals or fewer in all but eight of their final 35 games. Goaltender Jonathan Quick won the Conn Smythe as playoff MVP, and Los Angeles became the first-ever eighth seed to win a major North American championship.
No. 16 UMBC beats No. 1 Virginia
Virginia entered the NCAA Tournament with the nation's stingiest defense, a 31-3 record, and the ACC's top seed. UMBC had won the America East Tournament to sneak into March Madness as a 16-seed, a group that had gone 0-135 all-time against 1-seeds.
The teams were tied 21-21 at halftime, and then UMBC's offense exploded, outscoring Virginia 53-33 in the second half alone, more points than the Cavaliers had allowed in 15 full regular-season games. It remains the only 16-over-1 upset in tournament history.
Honorable mentions
A few upsets didn't have clean, verifiable odds to slot into the ranked list above, but they're too significant to leave out entirely.
New York Jets win Super Bowl III (1969)
The Jets entered as 17 to 18-point underdogs, a number so lopsided that spreads that size are essentially unheard of in the Super Bowl era. Joe Namath's guaranteed win backed up a stunning 16-7 upset, the first Super Bowl win for the AFL over the NFL, and arguably the single most consequential upset in American sports betting history. Betting in that era ran almost entirely through point spreads rather than moneylines, so no precise odds figure exists for direct comparison to the rest of this list.
USA pulls off "Miracle on Ice" (1980)
A team of American college players beat the heavily favored Soviet squad, widely regarded as the best hockey team in the world at the time, 4-3 in the medal round before going on to win gold. It's one of the most iconic moments in U.S. sports history, but Olympic hockey in 1980 wasn't priced by sportsbooks the way modern events are, so any odds figure attached to it today is a retroactive estimate rather than a documented closing line.
Matt Serra knocks out Georges St. Pierre (2007)
GSP entered as a -1300 favorite defending his welterweight title for the first time against Matt Serra. Serra clipped St. Pierre behind the ear with an overhand right, rushed him with a flurry of follow-up punches, and finished the fight via first-round knockout to claim the title.
Cleveland Cavaliers win NBA title (2016)
Down 3-1 to a record-breaking 73-win Warriors team, a deficit no team had ever overcome in NBA Finals history, Cleveland's odds fell to +1100. LeBron James and Kyrie Irving became the first duo to each score 40-plus points in the same Finals game in Game 5, James followed with 41 in Game 6, and Cleveland closed it out with a 93-89 win in Game 7 to complete the comeback and deliver the city's first major title in over 50 years.
