Rafael Nadal, Nick Kyrgios advance into Wimbledon men's quarterfinals

Everything went smoothly for Rafael Nadal against Botic Van De Zandschulp on Monday until it came time to close out their fourth-round match at Wimbledon.

Serving for the win at 5-3 in the third set, Nadal was broken for the second time in the match and he then failed to convert three straight match points when leading 6-3 in the ensuing tiebreaker.

That was the end of the Dutchman's resistance, though, as Nadal converted his fourth match point for a 6-4, 6-2, 7-6 (6) win on Centre Court. The Spaniard is playing his first grass-court tournament since 2019, when he lost to Roger Federer in the Wimbledon semifinals. He is looking for his third Wimbledon title and has a chance at a calendar-year Grand Slam after winning the Australian Open and French Open to take his career tally to a record 22 major titles.

Nadal will next face 11th-seeded Taylor Fritz, the only American man left in the draw.

Nick Kyrgios, meanwhile, is returning to the Wimbledon quarterfinals for the first time since making his debut in 2014 after improving his record in five-set matches at the All England Club to 6-0. Kyrgios overcame an ailing shoulder and a fourth-set slump to beat 20-year-old American Brandon Nakashima 4-6, 6-4, 7-6 (2), 3-6, 6-2.

Kyrgios needed treatment on his right shoulder several times during the match and was broken two straight times in the fourth set.

But he raced out to a 5-1 lead in the fifth and converted his first match point with a forehand volley. Despite the troublesome shoulder, Kyrgios finished with 35 aces.

And there was little in terms of antics or arguments from the Australian, unlike his previous match against Stefanos Tsitsipas, when he repeatedly argued loudly with the chair umpire and was accused by his