Top 10 Jaw-Dropping Moments in Tennis History

Tennis is an unpredictable game at the best of times. Throughout the sport’s history, it has provided more than a few jaw-dropping moments, feats of superhuman skill, stamina, and pure talent. Other moments are remembered for less than appealing reasons. Regardless, many have been so significant that they left a lasting mark, for better or for worse. 

1. Roger Federer Vs Rafael Nadal, 2008: One of the Best You'll Ever See

It's not often that a match is hailed as the greatest of all time. In 2008, at the Wimbledon Championship Final in London, Roger Federer and Rafael Nadal delivered a performance that truly lived up to the hype. Their masterclass of tennis is widely regarded as one of the best matches in the sport's history.

The friendly rivalry was already well documented, so expectations were high when they took to the court again on July 6. After winning two sets each, the pair went to an epic tiebreaker just like Borg and McEnroe before them. The pair traded shots for hours; by the end, just as the match clock hit 4 hours and 48 minutes, Nadal had won. 6-4, 6-4, 6-7 (5-7), 6-7 (8-10), 9-7.

Nadal had finally toppled his rival and won his first Wimbledon title, while Federer had been denied a sixth consecutive title win. Roger Federer and Rafael Nadal’s 2008 match is a good contender for one of the best and most unforgettable games in tennis history.

2. Novak Djokovic Vs Everyone: An Unbelievable 2023

Novak Djokovic has done more than enough to go down as one of the best tennis players, with a laundry list of achievements and accolades. However, in 2023, the Serbian certainly put an exclamation point on that fact. He matched the all-time Grand Slam record with 24, had victories in a trio of majors, 56 match wins, seven total titles, and a record eighth finish as the year-end world No.1.

3. Venus Williams Vs Serena Williams, 2017: 23 Grand Slams

The Williams sisters are two of the most dominant players the women's division has ever seen. Serena in particular has dominated the tennis world since her first singles Grand Slam and World No.1 ranking in 2002.

She has since won 23 Grand Slams in the singles division, the second most in history, behind Margaret Court. She achieved this feat in a 2017 match against sister Venus. After taking her 23rd Grand Slam title, 6-4, 6-4, Serena forever etched her name into the history books as one of the best of all time.

4. Marketa Vondrousova Vs Ons Jabeur, 2023: Yet Another Underdog Story

Sick of underdog stories yet? Good, because here’s another one. Marketa Vondrousova made history in 2023 after emerging as the first unseeded player in the Professional Era to win the Wimbledon women's singles title.

Vondrousova was ranked No. 42 and wasn’t seen as a serious contender. She quickly proved otherwise, taking down everyone in front of her. She wasn't supposed to win but she emerged victorious over Tunisia's Ons Jabeur in the final 6-4, 6-4 to become the first unseeded player in the Professional Era to win the Wimbledon women's singles title.

5. Emma Raducanu Vs Leylah Fernandez, 2021: Another Underdog Story

British tennis player Emma Raducanu might not have the same level of household recognition as Moneymaker, but she left her own mark on tennis in similar circumstances. She won entry into the 2021 US Open as a qualifier by competing in a pre-tournament qualifying competition. Raducanu was 18 at the time and expected to lose very quickly, as she was facing far more experienced opponents. To the surprise of everyone, she instead thrived, winning every match.

In the final, Raducanu beat Leylah Fernandez without dropping a set during the whole tournament. She became the first qualifier in the Open Era to win a major singles title. It was the second major tournament of her career. She still holds the Open Era record for the fewest majors played before winning a title. Raducanu was also the first British female US Open champion since Virginia Wade in 1968.

6. Bobby Riggs Vs Margaret Court and Billie Jean King, 1970s: Battle of the Sexes

In the 1970s, women's tennis was dominated by Billie Jean King and Margaret Court, two of the best female players to ever hit the court. At this time, self-proclaimed tennis hustler Bobby Riggs was on the lookout for any way to make a few dollars. He had been a top-notch player himself but had retired in 1951.

After Margaret Court played Riggs and lost, Billie Jean King challenged him to a match, which took place on September 20, 1973, at the Astrodome in Texas. King beat Riggs, a match watched by over 140 million people worldwide, which became a significant moment for women’s tennis.

7. Svetlana Kuznetsova Vs Francesca Schiavone, 2011: A Marathon of Top-Notch Tennis

In 2011, at the Australian Open in Melbourne, Australia, during the Open Women's Singles tournament, Svetlana Kuznetsova and Francesca Schiavone put on a show that became one of the longest tennis matches ever.

Each player won a set. When the third started, it didn't finish for a massive four hours and 44 minutes. Both Kuznetsova and Schiavone reached the brink of exhaustion and still kept going until Francesca Schiavone finally won the third set, 16-14.

8. Monica Seles Vs Magdalena Maleeva, 1993: A Dark Day for Tennis

During a 1993 quarterfinal match of the Citizen Cup in Germany, an incident occurred that is widely considered one of the worst to ever happen on a tennis court.

At the time, Monica Seles was ranked No.1 in the world and had been dominating the women's tennis division for two years. During a break, she was stabbed by a fan of Steffi Graf. The injuries weren't life-threatening, but the psychological damage deeply impacted Seles' promising career.

9. Pete Sampras Vs George Bastl, 2002: An Underdog Takes Down a Legend

On June 24, 2002, during the second round of the Wimbledon Championships, tennis experienced yet another classic underdog story. Pete Sampras was paired up against George Bastl, who was ranked No. 145.
Against all odds, Bastl won, defeating Sampras in a match that took place on Wimbledon’s court two, known as “The Graveyard of Champions.”

10. Bjorn Borg vs John McEnroe, 1980: One of the Greatest Matches Ever Played

In the 1980 Wimbledon Championship Tournament, Bjorn Borg and John McEnroe faced off in a match still remembered as one of the best displays of tennis ever.

McEnroe claimed the first set, but Borg fought back in the next two, leading to a legendary tiebreaker. Ultimately, McEnroe took the match, claiming his fifth and final Wimbledon crown.