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How ‘Qualifier’ Novak Djokovic Once Almost Pulled Off Greatest Tennis Upset Against Roger Federer in Monte Carlo Masters

Tanmay Roy
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4 Best Roger Federer vs Novak Djokovic Matches On Clay of all-time ft. French Open 2011 semifinal

With the Monte Carlo Masters 2024 impending upon us, let’s take a stroll back memory lane to the 2006 edition when Roger Federer faced Novak Djokovic for the first time in his career. Novak Djokovic came in as a qualifier, just beginning to rise in the tennis world. Roger Federer was already taking over the world and was the top-seeded player in the competition. Although it may seem like a match of equals today, at the time a Federer vs Djokovic was merely a David vs Goliath contest.

Rightly so, it was Roger Federer who won, but Novak Djokovic showed glimpses of his genius on that day, which would soon take over the world. He almost pulled off an incredible heist, stealing a win from Federer. But it was not to be on that day.

It was the first-round match in the Monte Carlo Masters 2006 match between the two giants of tennis, and Federer beat Djokovic in an evenly-fought contest. Djokovic had no answers to Federer’s shots in the first set. The then-18-year-old was still finding ways to fend off the Swiss great’s shots and eventually lost the set 3-6.

However, Djokovic came back very strongly in the next set. He started to pick Federer’s best shots, which in turn forced the Swiss player to make unforced errors. With errors piling on, Federer soon lost track of the plot and lost the set 2-6. However, Federer did not make the same mistakes in the final decider set and won it 6-3.

Federer won the match 6-3, 2-6, 6-3 and advanced to the next round. They met 49 times after that (50 in total) with Federer winning 22 and Djokovic winning 27 out of them. After the match, the commentator on air had a few praiseworthy words reserved for Djokovic.

He said, “He will have learnt an awful lot as he departs. And I’m sure we will see an awful lot of him in the future.”

The commentator couldn’t have been more accurate. Little did the world know then, as Djokovic walked off the court signing autographs for young kids, that this 18-year-old from Serbia will take over the tennis world in the future. His rivalry with Federer only intensified with the 2006 Davis Cup encounter and the 2008 Australian Open matches which followed.

Will Novak Djokovic be available for the 2024 Monte Carlo Masters?

Novak Djokovic had a not-so-merry run at this year’s tennis tournaments so far. The World No.1 player lost out on the Australian Open in the semi-final to Jannik Sinner and suffered a shock loss to Luca Nardi in Indian Wells. This was before his even more shocking announcement to skip the Miami Open.

Now, having split from long-time coach Goran Ivanisevic, fans expect to see a renewed Djokovic on the court. But whether it will be at the Monte Carlo Masters is the real query. Djokovic’s name is there on the roster for the Roqueburne-based Masters tournament.

As per the list, Novak Djokovic will enter the Monte Carlo Masters as the top seed, followed by Jannik Sinner and Carlos Alcaraz. He was practicing on the red dirt of Belgrade ahead of the clay season, which starts with the Monte Carlo Masters. With the necessary break in between, Djokovic will set his eyes on the prize, a chance to win the 3rd Monte Carlo Masters title of his career. While Rafael Nadal might also avail himself for the tournament, it could be a clash for the ages if both of them are in the same half of the draw.

Post Edited By:Dhruv Rupani

About the author

Tanmay Roy

Tanmay Roy

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Tanmay Roy is a Tennis Journalist at The SportsRush, whose lifelong passion and zeal for the sport landed him this position. A writer with over 1000 articles under him, Tanmay fell in love with tennis in 2005 when Roger Federer defeated Andy Roddick in the Wimbledon final after a stunning three sets. Tanmay followed the likes of the Big Three - Roger Federer, Novak Djokovic, and Rafael Nadal from the mid-noughties to now. His interest was stronger than ever after the wonderful 2009 Wimbledon Final which saw Roger Federer win after a see-saw 5-set match. His favorite female tennis player is Serena Williams and Monica Seles. Tanmay's favorite match-up to date is Roger Federer vs Andy Roddick in the 2000s. If possible, the John Isner vs Nicolas Mahut first round match at the 2010 Wimbledon is the only match Tanmay would love to watch Live by going back in time. Of late, he is a huge fan of Jannik Sinner and believes the youngster has the potential to break every record.

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