What sets the stage for an upset in tennis? Is it the stakes surrounding a given match? Is it the sheer difference in talent between the two players? Does there need to be a specific storyline at play?

All Wimbledon players, regardless of their stature, face the looming threat of being upset by a lower-seeded player every year. If there weren’t any upsets, the sport wouldn’t be very entertaining for tennis fans, would it?

Ranking the Top 10 Biggest Upsets in Wimbledon History

  1. 2022 Men’s Round of 16: Jannick Sinner defeats Carlos Alcaraz

Closing betting line: Sinner +230
Match Result: 6-1, 6-4, 6-7 (8-10), 6-3

Just as we did in listing the 10 biggest upsets in French Open history, we’ll kick off our Wimbledon list with a pair of recent surprises.

Although 20-year-old Jannick Sinner, the No. 10-seeded Italian, was two years older than Spanish teenager and No.5 seed Carlos Alcaraz, this was considered the upset of the 2022 tournament -- especially when viewed in hindsight. It was Alcaraz’s first ever Round of 16 at a Grand Slam event, but he was on a massive upward trajectory that would lead to a 2022 U.S. Open victory and a semifinal berth in the 2023 French Open. Wimbledon was supposed to be his first step.

Sinner was victorious in four sets. According to the ATP: “The fourth-round matchup between two of the brightest talents on the ATP Tour was the youngest match (in terms of combined age) at Wimbledon in the Round of 16 or later since 17-year-old Boris Becker defeated 21-year-old Henri Leconte in the quarterfinals in 1985.” Not a bad way to start this list.

  1. 2022 Women’s Third Round: Alize Cornet defeats Iga Swiatek

Closing Betting Line: Cornet +400
Match Result: 6-4, 6-2

One must understand how dominant current Polish world No. 1 Iga Swiatek has been over the past year and change to recognize the magnitude of this loss. Swiatek has been victorious at the last two French Opens, was champion at the 2022 U.S. Open, and carried a stunning 37-match win streak into Wimbledon in 2022 -- the 12th longest streak of any woman in the Open era.

World No. 37 Alize Cornet had this to say after winning: “ I can’t believe I’m the one who actually broke the streak.” Will Swiatek, in her sparkling current form, avenge her 2022 loss? Check out the 2023 women’s Wimbledon singles odds here.

  1. 2013 Women’s Fourth Round: Sabine Lisicki defeats Serena Williams

Closing Betting Odds: To win Wimbledon outright, Williams entered 1-2
Match Result: 6-2, 1-6, 6-4

World No. 1 Serena Williams entered her date with 23rd-seeded Sabine Lisicki on a 34-match winning streak that included the 2013 French Open championship. Remarkably, Lisicki had defeated a defending French Open champion at the previous three Wimbledon tournaments.

Against Williams, she would make it four in a row. Lisicki wouldn’t stop there, storming all the way to the final to set up a surprising matchup against No. 15 seed Marion Bartoli. This was a tournament full of upsets, as only three of the top 10 seeds reached the Round of 16. Bartoli would take the championship. 

  1. 1975 Men’s Final: Arthur Ashe defeats Jimmy Connors

Match Result: 6-1, 6-1, 5-7, 6-4

The reigning champion, world No. 1, and heavy favorite in the 1975 Wimbledon final, Jimmy Connors was nine years younger than his opponent, Arthur Ashe. Ashe was no slouch himself as the No. 6 seed, but he was facing a man who had made the finals of the previous four Grand Slam events he had entered.

The match was not close: apart from a hiccup at 5-6 in the third set, Ashe comfortably cruised and became the first black man to win Wimbledon. “I always thought I would win because I was playing so well and was so confident,” he later said.

  1. 1991 Men’s Second Round: Nick Brown defeats Goran Ivanisevic

Match Result: 4-6, 6-3, 7-6 (7-3), 6-3

Former Croatian world No. 2 Goran Ivanisevic had a love-hate relationship with Wimbledon. Entering the 1991 edition as a rising star in the game, the tournament’s No 10 seed, and a reigning semifinalist, Ivanisevic had high expectations surrounding him.

He drew British wild card and world No. 591 (not a typo) Nick Brown in the second round. Brown rode the home crowd to three straight victorious sets after dropping the first. “I knew it was low, but…” he said about his ranking. Brown lost in the third round to end his deepest-ever Wimbledon run.

Ivanisevic would lose three Wimbledon finals in the 1990s, and it looked like his career was over by 2001. Entering 2001 as a wild card, he miraculously won the whole thing, becoming the first wild card to ever win a major tournament. Tennis can be weird in that way.

  1. 2013 Men’s Second Round: Sergiy Stakhovsky defeats Roger Federer

Closing Betting Line: Stakhovsky +4500 
Match Result: 6-7 (5-7), 7-6 (7-5), 7-5, 7-6 (7-5)

The Swiss former world No. 1 Roger Federer had advanced to the quarterfinals at 36 consecutive Grand Slam events prior to the 2013 edition of Wimbledon. He drew Ukrainian Sergiy Stakhovsky, ranked No. 113 in the world, in a second-round matchup that oddsmakers didn’t think would trouble their pockets.

The oddsmakers were wrong. The 27-year-old veteran Ukrainian claimed the first victory over a top-10 player in his career. All four sets went at least 12 games, and after winning the first, a frustrated Federer fell just short over the following three.

Stakhovsky was stunned by his own performance: "When you come here, Roger Federer is on the cover of the Wimbledon book,” he said. “You're playing the guy and you're playing the legend which is following him, who won it seven times. You're playing two of them. When you're beating one you still have the other who is pressing you. You keep thinking: Am I really beating him?"

Remarkably, this wasn’t even the biggest upset on the men’s side that year. The match ranked ahead of it on this list gets that honor.

  1. 2013 Men’s First Round: Steve Darcis defeats Rafael Nadal

Match Result: 7-6 (7-4), 7-6 (10-8), 6-4

The biggest upset in the 2013 Wimbledon men’s draw was accomplished by Steve Darcis, the Belgian ranked No. 135 in the world. This was the first of only two times in his career that Spanish tennis legend Rafael Nadal lost in the first round of a Grand Slam event.

Nadal was dealing with injury issues in 2013, but that didn’t stop the Spaniard from capturing his customary French Open title. Meanwhile, Darcis had lost in 12 of his 18 previous first-round matches at major tournaments. An early break in a decisive third set (after two tiebreaker victories) sealed the match for Darcis against the weakened clay-court king. “He deserves not one excuse,” said an embattled Nadal.

  1. 2003 Men’s First Round: Ivo Karlovic defeats Lleyton Hewitt

Match Result: 1-6, 7-6 (7-5), 6-3, 6-4

This match made tennis history as the first time in the Open era that the defending Wimbledon champion lost in the first round.

Australian Lleyton Hewitt had ascended to the No. 1 spot in the ATP rankings after his 2002 Wimbledon triumph and entered the 2003 tournament as one of the favorites. His first-round opponent was a 24-year-old late-bloomer, Croatian Ivo Karlovic, who was making his Grand Slam debut.

Hewittlew a set point at 5-4 in the second set and lost the subsequent tiebreaker. “The first set, I was completely scared. After I saw that I can beat him, I started to play better,” the 6-foot-11” Croatian explained.

Hewitt would never win another Grand Slam event.

  1. 1999 Women’s First Round: Jelena Dokic defeats Martina Hingis

Match Result: 6-2, 6-0

From 1996 to 1999, Swiss world No. 1 Martina Hingis made the semifinals (at least) of every Grand Slam event she entered. At Wimbledon in 1999, her first-round opponent was Australian 16-year-old Jelena Dokic, a qualifier ranked No. 129 in the world.

Hingis, only 18 herself at the time, completely collapsed after taking a 2-1 first-set lead. She went on to drop 11 straight games. “I can’t believe I’ve beaten her,” said Dokic

The Swiss star had to retire at age 22 due to lingering injuries (before multiple comeback attempts), and never won a Grand Slam event after 1999. 

  1. 1994 Women’s First Round: Lori McNeil defeats Steffi Graf

Closing Odds: McNeil 100-1
Match Result: 7-5, 7-6 (7-5)

Between 1985 and 1994, Steffi Graf reached at least the quarterfinals of every Grand Slam event she entered. That streak came crashing down at Wimbledon in 1994.

The three-time defending Wimbledon champion drew American Lori McNeil in the first round. McNeil was no slouch herself, having been a 1986 Wimbledon quarterfinalist. However, she was literally a 100-1 shot to knock off Graf, who was probably the most dominant player in the history of women’s tennis.

On a day with rainy conditions, Graf was defeated by sloppy play late in both sets. Why should this match rank No. 1 on our top 10 list as the biggest upset in Wimbledon history? Let the headline from the following day’s New York Times explained: “McNeil Ousts Graf in an Upset for the Ages.”

Parameters of Rankings

Rankings were based on the degree of surprise in the result, the legacy of the given match, and the seeding difference between players.

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