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Biggest Betting Upsets In American History

August 22, 2023

Sports fans love an upset.

March Madness captivates us every year as we await a Cinderella to emerge. We wait for a longshot horse to win the Kentucky Derby, or a crushing hook to land a shocking knockout blow for an unexpected boxing title. Of course, the betting world also pays particular attention to teams with longshot odds in the hopes of striking it rich on one big hit.

Let’s run through some of the biggest upsets in American sports history. We may have left out some of your favorites — but a lot of memorable upsets loom large in the minds of sports fans.


US Hockey Shocks Soviets

“Do you believe in miracles? Yes!” There’s only one place to start with iconic upsets and that’s with the United States men’s hockey team taking down the mighty Soviet Union in the finals of the 1980 Winter Olympics.

Priced at +100000 to win gold, placing $100 on the stars and stripes at the beginning of the tournament would have netted bettors a tidy $100,000. This remains the archetype of the David vs. Goliath storyline, as the American roster was full of amateur players while the Soviet Union roster was littered with professional players that had extensive Olympic experience.

Add in the implications of the Cold War, and this win is forever etched in American history books and popular culture.

Rich Strike Was Surely That

We’ll shift to a more modern upset and turn to the 147th Kentucky Derby, which took place in 2022. Rich Strike entered with +8000 odds but hung around the top of the pack for much of the race before running along the inside rail down the final stretch to jump ahead of Epicenter and Zanden – both of whom were among the favorites in the field.

Rich Strike was the horse with the longest odds of the 2022 field entering the race and is among the biggest longshots to ever win at Churchill Downs.

Iron Mike Gets Bustered

We’ll next step into the ring and back in time to when Mike Tyson was known for his ferocity as a boxer rather than his cameo in The Hangover or a face tattoo.

In 1990, he entered his bout with Buster Douglas as a significant favorite to retain the title as heavyweight champion of the world, as Douglas had +4200 odds of victory. For reference, Tyson entered that matchup with a record of 37-0 with 33 knockouts, and he nearly added Douglas to that list in the eighth round when he brought him to a nine count on the mat.

However, Douglas persevered and shockingly knocked Tyson out for victory in the 10th round after a series of jabs and powerful uppercuts.

That fight ended Tyson’s reign of dominance over the sport, though Douglas failed to build on the momentum of his big upset win and faded into obscurity quickly thereafter.

Appalachian State? Seriously?

The 2007 college football season doesn’t look all that unique based on the fact that LSU won the BCS National Championship. Focusing only there leaves out a lot of key context, including two of the biggest upsets in collegiate history.

Appalachian State got things started in Week 1, when they beat the Michigan Wolverines in the Big House after entering the game as 33-point underdogs.

The Mountaineers held the lead for much of the game, but Michigan made a furious second half comeback. It appeared that they would escape with a victory after forcing an interception late in the fourth quarter, however Appalachian State ran an impressive two-minute drill to kick the apparent game-winning field goal with 26 seconds remaining.

The drama wasn’t done there though, as the Mountaineers needed to block a short field goal attempt by Michigan as time expired to become the first FCS squad to defeat a Division I team.

Harbaugh Beats Carroll

About a month later, the 1-3 Stanford Cardinal took the field against the 4-0 USC Trojans as 41-point underdogs. Stanford was relying on backup quarterback Tavita Pritchard, who had never started a game before and had attempted only three passes in his college career prior to the matchup.

Despite that lack of experience, Pritchard led the Cardinal to a 17-point fourth quarter, highlighted by a game-winning touchdown pass from 10 yards away, to defeat the Trojans 24-23.

USC went on to also lose to Oregon and finished the season ranked fifth overall after entering the season as the favorite to win the national title. The Cardinal closed the campaign with a 4-8 under first-year head coach Jim Harbaugh.

Fairleigh Dickinson’s Sean Moore (11) and Joe Munden Jr. (1) celebrate after the No. 16 seed Knights upset No. 1 seed Purdue in the NCAA Tournament on March 17, 2023. (Copyright: Scott Stuart)(IMAGO/PCN Photography)

2023 Was Fairleigh Amazing!

We’ve seen the gulf of talent between the major conference basketball programs and the mid majors close in the last several seasons. NIL money has leveled the playing field further, and we saw one of the most upset-filled NCAA tournaments in recent memory conclude this month.

The signature upset of the 2023 tournament was 16th seed Fairleigh Dickinson (FDU) taking out top seed Purdue by a score of 63-58. FDU was a 23.5-point underdog and they had Moneyline odds of +2100, while the Boilermakers entered the tournament with +1000 odds to win the whole thing.

A Very Sweet 16

While FDU is the most recent Cinderella, we can’t close the article without looking back on the first time a 16-seeded team beat a top seed. That took place in 2018 when the UMBC Retrievers took down the University of Virginia by a comfortable 74-54 margin.

The Retrievers entered the game as +2000 underdogs. Unfortunately, their Cinderella story ended one round later when they were eliminated by Kansas State by a score of 50-43.

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