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

#1 Robin Söderling

French Open 2009 Quarterfinal – def. Rafael Nadal 6-2, 6-7 (7-2), 6-4, 7-6 (7-2)

Robin Söderling produced the most incomprehensible upset in French Open history

This was the third Grand Slam encounter between the two. In the previous clash at Wimbledon 2007, Söderling lost a hard fought five-setter which lasted for four days owing to rain delays.

This match looked like a foregone conclusion; everyone assumed Nadal would tame his opponent in straight sets. But it turned out to be something entirely different for the Spaniard.

Söderling broke Nadal twice with his potent groundstrokes to win the opening set 6-2. The second set went to a tie-breaker in which Nadal took an unassailable 6-0 lead; he won it on his third set point after Söderling sent his forehand long.

The Swede broke Nadal's serve again mid-way through the third set and held his remaining service games to win it 6-4.

The fourth set went to a tie-breaker after both players exchanged breaks early on. Soderling dominated Nadal in the breaker and raced to a 6-1 lead. At 6-2, Nadal tried a drop shot which landed wide, and it was utter jubilation for Söderling - who became the first player ever to beat Nadal at the French Open.

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French Open 2010 Quarterfinal – def. Roger Federer 3-6, 6-3, 7-5, 6-4

Federer lost his way after the rain delay

A year after Federer scripted his maiden French Open triumph in 2009, he was up against the same but a more rejuvenated opponent. Federer won the previous encounter against Söderling in straight sets at Wimbledon 2009.

In the opening set, Federer took control by staying on the baseline and executing a few wonderful drop shots. It was in the eighth game, at 4-3, when Federer's delightful drop shot drew an error from Söderling to bring up a break point. Federer converted it as a Söderling volley sailed wide, and served out the set.

In the second set, both players primarily operated from the baseline, but Söderling started to attack Federer by venturing to the net. This strategy helped him save a critical break point in the opening game of the set. In the following game, Söderling's return of serve and forehand started to do some serious damage as he broke Federer and then went on to serve it out 6-3.

In the third set, the turning point came when Federer had a set point at 5-4 on Söderling's serve. It was a dramatic point, as Söderling ran towards the net and went for a smash volley; it appeared that he had saved the set point, but Federer cheekily sprinted behind the baseline to bring the ball back in play. But it was a fruitless attempt, as Söderling had the empty court to place the ball anywhere he liked, which he did.

At 5-5, there was a slight rain delay, which ended up breaking Federer's rhythm. He double-faulted to give a break point to Söderling, who happy obliged by whacking a forehand winner to get the break. He successfully served out the set and won it 7-5.

In the fourth set, Federer broke Söderling to take a 2-0 lead, but was immediately broken back. The match then had another momentary rain delay. Once play resumed, Federer started to commit unforced errors which allowed Söderling to get a vital break.

The Swede served for the match and held, to book his place in the semi-final of 2010 French Open final.

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Honorable Mention

Marin Cilic

Australian Open 2018 Quarterfinal – Nadal retired 3-6, 6-3, 6-7 (7-5), 6-2, 2-0

US Open 2014 Quarterfinal – def. Roger Federer 6-3, 6-4, 6-4

The reason Marin Cilic wasn't included in the list is that although he officially won the match, he did not completely stop Nadal. It was Nadal's injury that forced him to retire from the match.