5 players Federer has met in the highest number of different tournaments
During the course of his illustrious 22-year professional career, Roger Federer has met many an opponent - 344 of them to be precise. 233 different players have never managed to beat Federer, with matches against this group (582) accounting for almost 50% of the Swiss maestro's career win tally of 1237.
Of the remainder, only 26 players, seven of whom are active, have a winning head-to-head record against the record 20-time Grand Slam champion. Evgeniy Donskoy (2017 Dubai 3R), Thanasi Kokkinakis (2018 Miami 2R) and Andrey Rublev (2019 Cincinnati 3R) are the only active players, with one win apiece, never to have lost to Federer.
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In Grand Slam tournaments, where Federer (357) has the most wins of any player in the Open Era, Novak Djokovic and Rafael Nadal (10 apiece) lead a small group of 8 players to have beaten the Swiss maestro on multiple occasions. 26 other players have beaten Federer only once in Grand Slams, the last two being Stefanos Tsitsipas (2019 Australian Open 4th Round) and Grigor Dimitrov (2019 US Open Quarterfinals).
Djokovic is the only player to beat Federer at all the four Grand Slam tournaments, completing the set with a victory over the Swiss maestro in the 2014 Wimbledon final.
On that note, let us have a look at 5 players whom Federer has faced in the highest number of different tournaments.
#5 Stan Wawrinka - 16 tournaments
Federer has met his good friend and compatriot Stan Wawrinka in 26 matches across 16 different tournaments, overwhelmingly dominating their head-to-head rivalry 23-3. All 3 of Wawrinka's wins over his illustrious compatriot have come on clay - 2009 Monte Carlo Round of 16, 2014 Monte Carlo final and 2015 Roland Garros quarterfinal.
Excluding the Olympics, Federer has faced Wawrinka in all 5 tournament categories - Grand Slams, ATP Finals, Masters 1000, ATP 500 and ATP 250.
One of 8 opponents he has faced at all 4 Grand Slam tournaments, Federer has also played Wawrinka at the season-ending ATP Finals, Masters 1000 (7 tournaments), ATP 500 (Basel, Dubai, Rotterdam) and ATP 250 (Stockholm).
The most meetings (4) between the pair have occurred at the French Open (Federer leads 3-1) and Indian Wells (Federer leads 4-0). Monte Carlo is the only tournament where Federer has failed to beat Wawrinka, going 0/2 against the three-time Grand Slam titlist.