Venus Williams was stunned by Coco Gauff in the first round of Wimbledon last year. (Getty Images)

Over the years, the opening round at Wimbledon has produced many dramatic moments: from shocking upsets to debuts that gave a glimpse of good things to come.

Here’s a look at five matches from the All England Club that have had an impact on the game as a whole and fit in line with tournament’s reputation as the sport’s most prestigious event. (All photos: Getty Images)

1

The Future Is Now

At Wimbledon in 2019, five-time champion Venus Williams lurked in the draw as one of the most dangerous floaters the tournament had ever seen. Unseeded after a year of inconsistent results, the American faced her countrywoman Coco Gauff in the first round. Gauff—who, at 15 years old, was the youngest player to qualify for the main draw in the Open Era—pulled off the huge upset to kick off her run to the fourth round.

2

The Giant Giant-Killer

Stature-wise, Lleyton Hewitt and Ivo Karlovic resembled David and Goliath, respectively, but as far as accomplishments went, the roles were definitely reversed when the two faced off in 2003. Hewitt was the defending champion, while Karlovic was ranked 203 in the world and had battled through the qualifying rounds to make his main-draw debut at a major. The 6’10” Croat shocked the top seed in four sets, making Hewitt the first defending champ to lose in the first round in the Open Era.

3

A Future Champ in the Making

In 1998, Serena Williams had a solid start in her first year of playing the majors. Coming off a fourth-round showing at the French Open, the 17-year-old made her debut at Wimbledon a few weeks later and defeated Laura Golarsa in her opening match. Williams ended up making it to the third round in singles, but more notably, won her first grand slam title as she and Max Mirnyi took the top prize in mixed doubles.

4

The Start of Something Big

Having just turned 17 years old, Rafael Nadal was the youngest player in the 2003 men’s draw. The young Spaniard was also making his Grand Slam main-draw debut, and in the first round, defeated future top-tenner Mario Ancic in a battle of teenagers. Nadal won another match before his run came to an end in the third round, becoming the youngest player since Boris Becker in 1984 to make it that far. And like the German, Nadal ended up doing OK for himself at the tournament.

5

The Marathon—and Then Some

Going in, it was just another match on the schedule with the potential for an upset as John Isner, the 23rd seed, faced Nicolas Mahut, who was at his most dangerous on grass, at the 2010 tournament. What it turned out to be was a history-making affair as Isner won 70-68 in the fifth set to complete the longest match in history.