Biggest Upsets in Wimbledon History: Shock Exits for Nadal, Agassi, and Hingis Lead List

Coco Gauff became the first big-name casualty at the 2023 Wimbledon Championships, with the No. 7 seed losing in the first round to Sofia Kenin.

Wimbledon has seen its fair share of 'giant killings' in the past, with previous champions not immune to a shock defeat in the early rounds.

1. Steve Darcis defeats Rafael Nadal (2013)

No one expected Nadal to lose to Steve Darcis in the first round of the 2013 Wimbledon Championships. The Spaniard entered in a rich vein of form, reaching the finals in all nine events he participated in that year and winning seven of them.

Nadal was in the midst of a 22-match winning streak, with his last defeat coming against archrival, Novak Djokovic, in April. He was fresh off another victory at Roland Garros, lifting his 12th Grand Slam title in the process.

Darcis proved to be the ace's Kryptonite, however, handing the King of Clay the worst defeat of his career at the All-England Club. He recorded the biggest win of his career, defeating the two-time Wimbledon champion in straight sets, 7-6, 7-6, 6-4, per The Guardian.

The Belgian’s upset win was incredible because he entered that contest with just two victories in 2013. He also had just won one match at SW19 in his previous four tries.

To make Darcis’ feat even more astounding, he pulled that off with a shoulder injury, which forced him to withdraw before the second round.

2. Doug Flach defeats Andre Agassi (1996)

Andre Agassi entered his match against Doug Flach in the first round of the 1996 Wimbledon Championships as the overwhelming favourite.

He was the No. 3 seed in the tournament and was the top-ranked player in the world just four months earlier. On the other hand, Flach was ranked 281st and had to go through qualifiers to advance to the Wimbledon main draw.

Flach had suffered a horrible loss in his last Wimbledon match in 1995, losing 6-1, 6-2, 6-2 to 1,130th-ranked Guy Forget in the first round.

Tennis is a funny game, though, as he recorded the biggest win of his career, playing the match of his life against Agassi to pull off a 2-6, 7-6, 6-4, 7-6 upset win over the 1992 Wimbledon champion.

3. Jelena Dokic defeats Martina Hingis (1999)

Martina Hingis emerged as a dominant force in the final years of the 20th century, winning five Grand Slam titles from 1997 to 1999.

She entered the 1999 Wimbledon Championships as one of the favourites after winning the Australian Open earlier that year, yet she failed in her bid to win her second Wimbledon title after losing in the first round against Jelena Dokic.

The 129th-ranked player in the world recorded an upset for the ages, crushing Hingis 6-2, 6-0, in a match that lasted just 54 minutes, per WTA.

She blitzed past the Swiss star, winning the last 11 games for a comprehensive victory.

4. Ivo Karlovic defeats Lleyton Hewitt (2003)

Hewitt made the wrong kind of history in his match against Ivo Karlovic in the 2003 Wimbledon Championships, becoming the first defending champion in the Open Era to lose in the first round at the All-England Club.

Karlovic’s win was unexpected as he had won just two main tour matches in his tennis career prior to his meeting with Hewitt. This was also the first time he qualified for a Grand Slam event in 11 tries.

The 203rd-ranked player in the world made the most of this opportunity, coming back from a set down to record a stunning 1-6, 7-6, 6-3, 6-4 victory over Hewitt.

5. Peter Doohan defeats Boris Becker (1987)

Becker entered the 1987 Wimbledon Championships with dreams of winning his third consecutive title at the All-England Club.

The German star had every reason to feel confident of his chances, as apart from being the two-time defending champion, he was also the No. 1 seed for the first time at Wimbledon.

Becker and Doohan faced each other at Queen’s Club weeks before their Wimbledon meeting, with the 19-year-old winning in straight sets in that match. He went on to win that grass-court warm-up event, setting the stage for another title run at SW19.

On the other hand, Doohan entered his match against Becker with a paltry 1-4 record at Wimbledon, with his lone win coming in the first round of the 1987 tournament. That victory instilled belief in Doohan that he could record a major shock against Becker.