5 players who have defeated both Roger Federer and Rafael Nadal in Grand Slams

#3 Juan Martin Del Potro

US Open 2009 Semifinal - def. Rafael Nadal 6-2, 6-2, 6-2

It was a gruesome loss for Nadal

In 2009, Juan Martin del Potro rose to prominence by reaching the French Open semi-final where he lost to Federer in a five-setter. But at the US Open that same year, he did something truly incredible: he become the first player to beat both Nadal and Federer in the same Grand Slam.

In the semi-final, Nadal had no answer to Del Potro’s stroke play which produced some outstanding winners and also drew errors from the Spaniard. As a result, Nadal suffered his biggest margin of defeat in a Grand Slam match.

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US Open 2009 Final - def. Roger Federer 3–6, 7–6(7–5), 4–6, 7–6(7–4), 6–2

Del Porto won his first grand slam at the age of twenty

Del Potro had not forgotten the defeat at the hands of Federer in the 2009 French Open, and was looking for redemption.

Federer started the match on the offensive by breaking Del Potro early on and won the first set 6-3. He was serving for the second set at 5-4 but Del Porto broke back and took the set to a tie-breaker, ultimately winning it 7-5.

Federer won the third set after breaking Del Potro’s serve at 5-4, and had multiple break point opportunities in the fourth set but couldn’t convert them. The set went to a tie-breaker again which Del Potro won after Federer committed a few unforced errors, including an untimely double fault.

In the fifth set, Federer looked a bit fatigued and was broken in his opening service game. His stroke play became iffy after that, and he couldn’t mount a comeback as Del Potro went on to win the fifth set 6-2.

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Bonus Mentions

US Open 2017 Quarterfinal – def. Roger Federer 7-5, 3-6, 7-6(10-8), 6-4

US Open 2018 Semifinal – Nadal retired 7-6 (7-3), 6-2