4 Times Novak Djokovic Lost Despite Having Match Points

Published 11/27/2023, 2:09 AM EST

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via Reuters

Tennis legend Novak Djokovic, in his journey to 24 grand slam titles including the Career Golden Slam, winning all four majors, and the Olympic gold medal in singles, the legend has always been a symbol of consistency throughout the game. Sometimes, even the best players get to experience the effects of bad days. The traces of history have some matches when Djokovic, even after starting a match strongly and holding the odds in his favor, had to witness an unexpected defeat in the end.

Although situations like these are rare with the Serbinator, the tennis books keep track of every single match that is played professionally. These are the matches that stick in his mind and disappoint his fans. Here are four matches that ended up haunting both Djokovic and his fans, making him wish that he could have played differently.

2023 Davis Cup SF to Sinner


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Novak Djokovic, despite being the best tennis player in the world, is still not unbeatable. He learned that the hard way when he faced Jannik Sinner, the young Italian star he matched twice at the ATP Finals.

While the Serb stood against him once again at the Davis Cup semifinals, Sinner shocked Djokovic and the tennis world by beating him twice in one day, in two intense matches. The first match was a singles, where Sinner came back from a set down to win 6-2, 2-6, 7-5. He saved two match points in the final set and broke Djokovic’s serve in the last game.


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It was a stunning performance by Sinner, who showed no fear against the world number one. Sinner became the first player to beat Djokovic in a Davis Cup singles match since Juan Martin del Potro in 2011. He also became the first player to beat Djokovic twice in one day. It was a historic achievement for Sinner, who proved that he is a future star of the sport.

2018 Queen’s Final to Cilic

The 2018 Queen’s final between Novak Djokovic and Marin Cilic was nothing less than a complete pack of emotions for the spectators. Djokovic, who stood at the peak of his game, had the golden opportunity to hit the victory blows as he held match points against Cilic.

Everyone in the audience held their breath, waiting for the moment to jump off their seats and celebrate the win. However, the tennis gods had a different script in mind on that day. Showing an unexpected switch in form, Cilic turned the tables.

Djokovic, despite being quite ahead of the Croatian, couldn’t seal the deal and faced a defeat with a final score of 5-7 7-6(4) 6-3. As the match slipped away from the Serb’s firm grip, the moment left Djokovic and his fans in disbelief.

The defeat came out to be more than just a loss, but a lesson in the unpredictable nature of tennis matches, where even the greatest do not stand with a win guarantee.

2009 Madrid SF to Rafa

Another moment when Novak Djokovic lost despite having match points was marked during the 2009 Madrid semifinal against Rafael Nadal. This match came out to be a thrilling and exhausting one that lasted for more than four hours and ended with a dramatic tiebreak.

Djokovic started the match strongly as he easily managed to win the first set 6-3. He had a sure chance to break Nadal in the third game of the second set, but the Spaniard saved it with a powerful serve. The set went on with no breaks until the scoreboard said 4-4 when Djokovic had two more opportunities to take the lead. However, Nadal fought them off with some incredible defense and winners.

The set went to a tiebreak, where Djokovic had a set point at 6-5. He missed it with a forehand error, and Nadal took the next two points to level the match at one set all. The third set was also very close, with both players holding their serves until another tiebreak.

In the final tiebreak, Djokovic had three match points at 6-3, 7-6 and 9-8. Nadal then won the next two points to confirm the victory with 11-9 in the tiebreak. This was one of the most long-duration matches in tennis history and one of the most painful losses for Djokovic. Even after coming so close to beating Nadal on clay for the first time, he could not finish him off. Nadal, proving why he is the king of clay, went on to win the title in Madrid.


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2007 Rotterdam SF to Youzhny

This was one of the earliest disappointments for Djokovic, who was still a rising star at that time. He faced Mikhail Youzhny, a Russian veteran who was known to have a solid game on hard courts. Djokovic had two match points at 6-5 in the third set, but Youzhny saved them with some amazing defensive clutch shots. He then won the tiebreak and advanced to the final. Djokovic seemed to be really upset and threw his racket in anger.

These four times marked the unpredictability that tennis matches carry. The matches in which Novak Djokovic lost despite having match points show that even the best players can make mistakes under pressure and lose their focus. They also show that tennis is a sport of fine margins, where one point can make all the difference.


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However, the Serbinator learned from these losses and came up as a stronger player every time. He has also won many more matches where he saved match points himself, presenting strong proof to the world about his strength and excellence on the court.

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Written by:

Akshay Kapoor


One take at a time

Akshay Kapoor, a tennis writer at EssentiallySports, was born into a family that breathes Tennis and grew up watching the electrifying rallies of the legendary Rafael Nadal. Coming with a prior experience in Sports Journalism, he excels in crafting pieces that set new trends. His analytical skills riding on the back of certification in Digital Marketing help inject in-depth research as he covers the business undertakings of Tennis stars.
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Edited by:

Ananya Giri