#3 Novak Djokovic - 16 tournaments
With 49 meetings spanning across 16 tournaments and 13 years, no player has played Federer as many times as Novak Djokovic has. No player has also beaten Federer as many times (26) as Djokovic has, the most recent one being the pair's epic 2019 Wimbledon final where the Serb became the first winner at the grasscourt Major in 71 years to have saved multiple championship points.
Djokovic has also denied Federer on two other occasions from match points down - both such instances happening in the US Open semifinals (2010-11).
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One of only 8 players to face Federer at all four Grand Slam tournaments, Djokovic is the only one of the octet to beat the 20-time Major winner at the all four. Djokovic and Nadal with 10 wins apiece form the only pair to have beaten Federer multiple times in Grand Slam matches.
Djokovic and Federer have also clashed 6 times at the ATP Finals, with each player winning thrice apiece; that is the highest number of times they have met at any tournament. Federer and Djokovic have also met at all Masters 1000 tournaments except Madrid, and twice in ATP 500 tournaments (Basel and Dubai).
With 14 wins (also Nadal), no player has beaten Federer in as many tournament finals as Djokovic has - a tally which includes 4 Grand Slam finals.
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