Andre Agassi suffered a shock first round defeat at Wimbledon in 1996.
Agassi won his first Grand Slam title at Wimbledon in 1992, where he beat Goran Ivanisevic in the final.
The American had failed to return to another final at the grass court major since then, and Agassi was hoping to return to Grand Slam winning form again at Wimbledon.
However, instead of challenging for another major title, Agassi actually lost in the first round of Wimbledon for the first time in nine years.
Doug Flach beat Andre Agassi in the first round of Wimbledon in 1996
Agassi was the third seed at Wimbledon in 1996, and was the big favourite to win his first round match against qualifier Doug Flach.
Flach had never won a main draw match at Wimbledon before, and had only ever won one main draw match at a major, but gave himself an opportunity to do so after coming from two sets to love down in his final qualifying match.
Not only was there a big difference in rankings between Agassi and Flach, but the former had also won his only two previous meetings against the qualifier.
However, this did not matter at Wimbledon, as Flach stunned Agassi by beating him 2-6, 7-6(1), 6-4, 7-6(6).
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This was a second consecutive early Grand Slam defeat for Agassi, who had also lost in the second round of Roland Garros, and after the match he admitted he was not expecting a lot from his Wimbledon campaign.
“I wasn’t expecting a whole lot after not having played in a couple of months,” Agassi said at the time.
Agassi also called out the current tennis calendar, something that continues within tennis to this day in 2026.
“Something has got to be done for the game,” added Agassi. “Tennis needs to change the entire structure. It needs an off-season. It needs a ranking change. It needs to get people who know what the hell they are doing to be quite honest.”
Flach would go on to back his win over Agassi up in the second round, where he beat another qualifier in Jared Palmer, before losing in the third round to Thomas Johansson.
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What was Doug Flach’s career-high ranking?
This was the best ever Grand Slam result Flach would achieve in his singles career, and he was also never able to break inside the top 100.
Flach reached a career-high singles ranking of world number 108 in 1994, and he was never able to push on from this, even after his Wimbledon win over Agassi.
This was not even the only win Flach obtained over Agassi, having also beaten him in Washington D.C. in 1997.
Flach also beat the likes of Ivan Lendl, Pat Rafter and Gustavo Kuerten in his career, but he was still never able to break into the top 100.
The best results of Flach’s career came in doubles, where he won two ATP titles and achieved a career-high ranking of world number 73 in 1994.
Flach officially retired from tennis in 2001, with the American playing his last ever match in doubles in Atlanta.