Founded in 1877, the Wimbledon Championships are the oldest and, in fact, one of the most prestigious tennis tournaments in the world. Over the span of these 148 years, the tennis world has seen the rise of several superstars, but at the same time, it has also witnessed several setbacks and downfalls. This journey of ups and downs is what makes tennis so special, and this tournament even more special. Talking about this iconic grass-court tournament in 2021, the seven-time champion Serena Williams revealed that it’s always a “very special feeling” entering this lush green venue. Just like her, even the 2002 Wimbledon Champion, Lleyton Hewitt, claims it to be a “pretty special place” and winning the title here remains his most treasured tennis memory.

Other champions, like Steffi Graf (seven-time champion), had said, “Grass is a surface I have always loved; Wimbledon is a tournament I have always loved.” But amid all their fond memories, there lie a few setbacks that mark some of the biggest upsets in the tournament’s history. Let’s take a look at some of those matches from the past.

5. Peter Doohan beats defending champion Boris Becker in the R64 of the 1987 Wimbledon Championships

What did this tournament mean to someone like Boris Becker? Last year, while sharing his thoughts on this iconic grass court event, Becker said, “Wimbledon has been my favorite tournament as a player, coach, and commentator. It’s unique, you can’t compare it. It’s a part of my life. It’s in my DNA, you can’t deny that.” He won this tournament three times (1985,1986,1989) in his career, but his defeat to the Aussie in the R64 of the 1987 Wimbledon marks his most bitter memory at this tournament.

Doohan defeated Becker by 7-6(4),4-6,6-2,6-4 in that match, and following that impressive win against the ‘Boom Boom’ Becker, who was then on a 15-match winning streak at Wimbledon, reached a career-high of 43rd in the rankings. Since that match, Peter Doohan was dubbed the ‘Becker Wrecker’. What were their reactions after the match, though?

After the match, Doohan said, “I thought what a bad draw and started to think about plane reservations out of here.” While Becker stated, “It was not a war – it was a game of tennis and I lost. I’m not immortal; I knew I would have to lose some time at Wimbledon. Sometimes in this game it is sunny, sometimes it is cloudy.” This was one of the greatest upsets in Wimbledon history, but what comes up next?

4. Lori McNeil stuns Steffi Graf in the first round of the 1994 edition

Unseeded in the draw, Lori McNeil became the first player of the Open Era to beat a defending Grand Slam champion in the first round of their title defense. Having won three straight Wimbledon titles and reaching 31 consecutive major QFs, Graf was a clear-cut favorite before entering this contest. But the American had other plans! She defeated Steffi Graf by 7-5,7-6(5) in that epic battle.

While sharing her thoughts about this match in an interview (in 2014), McNeil said, “I felt comfortable playing her. She was an aggressive baseline player, but I knew I couldn’t beat her from there. I enjoyed coming to the net and our games matched up well. I had good feelings that day.” What was Graf’s reaction after this shocking defeat?

Steffi Graf said, “It doesn’t hurt to lose my crown, it hurts to lose.” It was her only loss at Wimbledon between 1991 and 1996. However, despite all her disappointments, Graf was quite respectful of her opponent’s historic feat. She said, “It’s not that big of an upset because of who I lost to.” 

3. Iva Karlovic defeating Lleyton Hewitt in 2003

It was their first meeting on the Tour, and the Croatian couldn’t have asked for a better start to their rivalry. He defeated the defending champion by 1-6,7-6(5),6-3,6-4 in the R128 of the 2003 Wimbledon Championships. Before this, no man had ever lost in the opening round of his title defense campaign at Wimbledon.

Reacting to this hard-fought battle, Karlovic later on admitted, “The first set, I was completely scared. After I saw that I can beat him, I started to play better.” The 2002 Champion, Lleyton Hewitt, claimed, “When I missed those opportunities early in the second set, his whole game sort of came together. He didn’t make as many easy mistakes.” This match also marks one of the biggest upsets in the history of this historic tournament. What else is on this list?

2. Serena Williams’ 2014 early round defeat since 2005

Having won the title seven times in her career (2002,2003,2009,2010,2012,2015,2016), Serena Williams‘ worst memory at Wimbledon was losing to the 24th in the world, Alizé Cornet, in the third round by 6-1,3-6,4-6. Williams was then desperate to equal Chris Evert and Martina Navratilova’s 18 Grand Slam titles record, but her dream came to a shocking end at the hands of the ‘Giant-Killer’. It was, in fact, only the third time in 15 visits to Wimbledon that Serena Williams had lost so early.

After this match, Cornet said, “I just cannot believe it. Three years ago, I couldn’t play on grass, I was so bad, but now I have beaten Serena, the world number one, on her own court.” Analyzing her poor performance in this match, Serena Williams said, “She kept her unforced errors really low. I made a few errors too many. She was going for her shots. She played really well.” Alizé Cornet has, in fact, labeled this match as the “biggest shock of the tournament“. 

However, after this shocking defeat, Serena Williams made a strong comeback and won the title in 2015 and 2016. But which match tops the list of biggest upsets in Wimbledon history?

1. Novak Djokovic beats 8-time champion Roger Federer in the longest Wimbledon singles final

In this match, the Serb had managed to save two championship points to secure a victory against the Swiss Maestro. Everyone inside the stadium was on the edge of their seats throughout this epic 4-hour and 57-minute battle. Novak Djokovic defeated Roger Federer by 7-6(5),1-6,7-6(4),4-6,13-12(3). Roger Federer, who was then chasing a record-equaling ninth Wimbledon singles title, was left in utter disbelief at what had just happened at that time. After the match, Novak Djokovic said, “It’s quite unreal.“

Together, they’ve met each other 50 times in their careers, but this match stands tall among the biggest upsets for Roger Federer. Even years after this epic battle, both of them are often seen revisiting a few moments from this match. For example, Novak Djokovic once admitted, “It was a match in which he [Federer] was the better player statistically. He won more points, and he just had all the stats on his side. But I just found a way to win in important moments and to play the right shots at the right time. At 40-15 down, I just tried to make him play and make him earn his victory. He came to the net. I made a passing shot and second match point and he got tight a little bit and I used my momentum. Again it was a very close one very close match, probably the most nerve-wracking match I was ever part of.”

What was Federer’s reaction to this shocking defeat? After the match, he said, “I don’t know how I feel right now. I just feel like it’s such an incredible opportunity missed, I can’t believe it. It is what it is.” Even last year during an interview, he revisited that moment, saying, “I lost that match, but I think that if I had won, my life wouldn’t have changed anything. As a child, I dreamed of one day playing at Wimbledon Central and winning the tournament. I didn’t expect to win it eight times and have so much success around the world.” The War of 13-12 as they say!

Other than this, Roger Federer’s biggest upset at Wimbledon was losing to Sergiy Stakhovsky in the second round (R64) of the 2013 Wimbledon Championships. That defeat not only ended his title defense hopes but also ended his streak of 36 straight major QFs. Which, according to you, is the biggest upset at Wimbledon? Share your thoughts if you think we’ve missed out on any other epic setback at Wimbledon.