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Reading: Five of the most shocking upsets in sports history, from Michigan-App State to Virginia-UMBC
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Five of the most shocking upsets in sports history, from Michigan-App State to Virginia-UMBC

Last updated: May 29, 2026 6:49 pm
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Five of the most shocking upsets in sports history, from Michigan-App State to Virginia-UMBC
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The news of world No. 1 star Jannik Sinner’s improbable defeat at Roland Garros continues to send shock waves through the sports world, as the four-time Grand Slam champion was upended in the second round of the French Open.

Not only was he heavily favored to win the whole thing, he was up two sets to none and was winning a decisive third set 5-1 before choking the lead away in five sets, spoiling a 30-match win streak.

Sinner’s clay-court catastrophe will be remembered as one of the biggest tennis upsets of all time, but it got me thinking about some of the other .

Below are five of the most unbelievable “David vs. Goliath” moments in sports, where the unthinkable quickly became reality and reset the bar for what was possible from an underdog facing insurmountable odds.

I’m sure many of you will take exception with this list, so feel free to leave a comment below letting me know which upsets I missed.

In January 2017, Novak Djokovic was the closest thing to a god in the tennis world.

The Serbian superstar was fresh off a two-year run in which he won five of a possible eight Grand Slam tournaments and had just captured the first French Open title in his career in 2016.

Heading into the Australian Open, it was widely believed The Djoker would cruise to another tournament win on his surrogate home court, considering he had already won in Melbourne six times before.

In the second round, Djokovic squared off against 117th-ranked Denis Istomin, and much like Sinner, had a commanding two-set lead before blowing it in spectacular fashion.

By the time the dust had settled, Djokovic was packing his bags and heading home, marking the first time he exited the second round of a major championship in nearly a decade and the first time he had lost to a player ranked outside the top 100 in his illustrious career.

Djokovic’s 2017 was a tumultuous one, and his flameout at the Australian Open was the harbinger of a largely forgettable season.

The 2015-16 Golden State Warriors are a case study in how to have a historic year only to blow it the millisecond before crossing the finish line (though they aren’t the only ones to do so on this list).

After a record-breaking season in which the Warriors set the all-time regular season wins total at 73 and guard was awarded the only unanimous MVP in league history, all that was left was vanquishing a LeBron-led Cleveland Cavaliers team.

With a double-digit win in Game 4, Golden State took the now infamous 3-1 lead and looked to put the series on ice at home in Game 5.

Then it happened.

Defensive stalwart Draymond Green was suspended for accumulating too many flagrants, meaning he would miss game five, a game in which the Cavs blew the doors off of the Warriors in a 15-point win.

After another double-digit win in Game 6, it was obvious Cleveland had all the momentum in the world, and although Game 7 was one of the most tightly contested and memorable games in NBA Finals history, a Cavaliers series comeback felt inevitable.

No team had ever overcome a 3-1 deficit in the NBA Finals, and the fact that the Warriors won 73 regular season games made this even more shocking.

It was equally impressive that the Cavs were able to mount the comeback as it was embarrassing that the Warriors blew what was a “golden” opportunity to etch their names into the history books.

Heading into the 2007 season, the were heavy favorites to win the Big Ten and win a BCS National Championship.

The team was littered with veterans and hopefuls like Chad Henne, Jake Long and Mario Manningham, among others, and entered the year as a consensus top-five team coming off an 11-win season in which they narrowly missed playing for a national title.

They opened the season with FCS powerhouse Appalachian State, but no one was expecting much from the lowly Mountaineers as they traveled to the Big House to play the Maize

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