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Rafael Nadal was defeated by compatriot Carlos Alcaraz in the quarterfinals of last week's Madrid Masters. The three-set triumph saw the Murcian join a small group of players to have beaten the current World No. 4 before their 20th birthday.
Alcaraz followed up his quarterfinal victory with a close three-set win over the World No. 1 Novak Djokovic in the semifinals, before crushing Alexander Zverev to lift the title on Sunday.
On that note, here is a look at the seven teenagers who have scored a win over the 35-year-old Spaniard:
#1 Mario Ancic - Milan 2004
Nadal met Mario Ancic in the second round of the Milan Indoor tournament - a former ATP International event played on indoor carpet courts - in February 2004. The-then 17-year-old Spaniard held a 2-0 record against the Croat - who turned 20 the following month - heading into the match.
After an opening-round win over Ivo Karlovic, the No. 6 seed was downed 7-5, 6-2 by the unseeded Ancic, who went on to lose in the final to Antony Dupuis. The Mallorcan holds a 4-1 career head-to-head record against Ancic, who reached a career-high ranking of World No. 7 before his 2011 retirement.
#2 Tomas Berdych - Cincinnati 2005
At the Cincinnati Masters in August 2005, a 19-year-old Nadal faced a 19-year-old Tomas Berdych, who would turn 20 the next month. He had won his only previous match against Berdych in the Bastad final earlier that year.
The unseeded Czech upset the No. 2 seed 6-7(4), 6-2, 7-6(3) in the first round of the ATP Masters 1000 tournament. The Spaniard finished with a 20-4 record against Berdych when the former World No. 4 retired in 2019.
#3 Novak Djokovic - Miami 2007
At the Miami Open in March 2007, a 20-year-old Nadal met a 19-year-old Djokovic in the quarterfinals. The Mallorcan had won both of the pair's prior encounters, including the final of the Indian Wells Masters earlier that month.
Djokovic, seeded 10th, beat the No. 2 seed 6-3, 6-4, before going on to claim his first-ever ATP Masters 1000 title. The Serb currently holds a 30-28 head-to-head lead over the Spaniard from a men's Open Era record of 58 matches between the legendary pair.
#4 Nick Kyrgios - Wimbledon 2014
Nadal and Kyrgios faced off for the first time in the fourth round of the 2014 Wimbledon Championships in July 2014. The-then 28-year-old Spaniard was the World No. 1 but seeded second, while the 19-year-old Australian was making his Wimbledon debut as a wildcard.
Kyrgios, ranked 144th, stunned the two-time champion 7-6(5), 5-7, 7-6(5), 6-3 with a memorable performance, before losing to Milos Raonic in the last eight. The Mallorcan now holds a 6-3 record against the 27-year-old Australian.
#5 Borna Coric - Basel 2014 and Cincinnati 2016
Borna Coric is the only player to defeat Nadal twice as a teenager, with his first win coming at the Swiss Indoors in Basel in October 2014. The-then 17-year-old Croat, competing as a wildcard, upset the No. 2 seed 6-2, 7-6(4) in the quarterfinals of the ATP 500 event.
Coric then dismantled the third-seeded Spaniard in the third round of the Cincinnati Masters in August 2016, as a 19-year-old. The head-to-head series between the pair is currently tied at 2-2, with the 21-time Major champion earning wins over the Croat at the 2015 US Open and the 2017 Canada Masters.
#6 Denis Shapovalov - Montreal 2017
At the Canada Masters in Montreal in August 2017, an 18-year-old Denis Shapovalov faced Nadal for the first time. The Canadian, playing as a wildcard, produced an inspired display to upset the No. 1 seed 3-6, 6-4, 7-6(4) in the third round.
Shapovalov went on to reach the semifinals of the ATP Masters 1000 event, losing to eventual winner Alexander Zverev. The Spaniard has won all four of the pair's clashes since then, including a five-set battle at this year's Australian Open.
#7 Carlos Alcaraz - Madrid 2022
At the 2022 Madrid Masters last week, Alcaraz became the latest player to beat Nadal before turning 20. The 19-year-old's 6-2, 1-6, 6-3 quarterfinal triumph also saw him become the first teenager to ever beat his great countryman on a claycourt.
Alcaraz's epic three-set semifinal win over Djokovic then made him the first player to beat the iconic duo in the same tournament on clay. The World No. 6 currently holds a 1-2 record against Nadal and a 1-0 record against Djokovic.
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