No 1 Club
The first chapter of Djokovic-Federer: Monte-Carlo 2006
Serbian and Swiss faced off for the first time 20 years ago at ATP Masters 1000 event
April 07, 2026
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Novak Djokovic and Roger Federer in action in Monte-Carlo in 2006.
By Sam Jacot
Novak Djokovic’s prolific rivalry with Roger Federer is one of the defining storylines in 21st-century men’s tennis so far. The Serbian faced the Swiss star 50 times and finished with a 27-23 lead in their Lexus ATP Head2Head series.
But every rivalry has a beginning.
To find theirs, you have to rewind 20 years to April 2006 at the Rolex Monte-Carlo Masters. Federer, then firmly established as the No. 1 player in the PIF ATP Rankings, arrived in The Principality in dominant form. The Swiss had already claimed the ‘Sunshine Double’, titles at Indian Wells and Miami, for the second straight year, adding to his Australian Open crown and a trophy in Doha at the start of 2006.
Across the net in Monte-Carlo stood an 18-year-old Djokovic, ranked No. 67 and still searching for his first tour-level title. On paper, it looked routine for Federer, with Djokovic needing to earn two wins just to qualify for the main draw at the ATP Masters 1000 event. On court, it was anything but.
Federer took the opening set 6-3 but Djokovic responded, levelling the match 6-2 after the Swiss missed a forehand volley on set point. The decider ultimately went Federer’s way, yet the scoreline, 6-3, 2-6, 6-3, only told part of the story. Djokovic saved three match points before losing, pushing the top seed for one hour and 49 minutes and hinting at the resilience that would later define their rivalry.
Federer recognised that potential even then.
“I definitely think he’s a good player,” Federer said after the match. “He was alright from the baseline and everything. I think he’s still got many areas where he can improve, so there is some potential, absolutely.”
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Roger Federer in action against Novak Djokovic in Monte-Carlo in 2006. Photo: VALERY HACHE/AFP via Getty Images
Djokovic, meanwhile, viewed the encounter as a valuable learning experience.
“This will be a big experience for me and my confidence will grow up for sure after this match because I know that I played well,” Djokovic said. “I’m still young, so I just need to have more and more matches like this so I can learn how to play against these kind of players.”
That early resistance in Monte-Carlo proved indicative of their rivalry. Years later, Djokovic would famously fend off championship points against Federer in the 2019 Wimbledon final and overturn match points in dramatic US Open semi-final encounters in 2010 and 2011.
The 2006 meeting was just the opening chapter. Federer won their next three clashes before Djokovic earned his breakthrough victory in the Montreal final in 2007, marking the true arrival of a rivalry that would help shape a generation. In Monte-Carlo, Federer reached the final four times (2006, 2007, 2008, 2014) but never triumphed, while Djokovic is a two-time champion (2013, 2015).
