Three out of the four Indian tennis players in the qualifying draw of the US Open, the last Grand Slam of the year, went down in the first round after three-set battles on Tuesday night.

Ankita Raina, the only Indian in the women’s singles draw, lost to to Jamie Loeb 3-6, 6-2, 4-6. She made a comeback in the second set but was unable to hold on against a player ranked one place below her at world No 194. She made her Grand Slam debut in doubles at Australian Open and played both doubles events at Wimbledon, but is yet to play a singles match at a Major.

Sumit Nagal, who had made his Grand Slam debut at US Open in 2019 memorably against Roger Federer and won a match last year before going to down to eventual champion Dominic Thiem in second round, couldn’t get a direct entry into the main draw this year. The world No 165 went down 5-7, 6-4, 3-6 to the much lower ranked Juan Pablo Ficovich in two hours and 22 minutes.

Nagal had played in the Australian Open main draw early this year and had lost in the first round. He could not qualify for the French Open and missed the Wimbledon qualifiers due to an injury.

Later, Ramkumar Ramanathan went down fighting to the 30th seed and a former top-100 player Evgeny Donskoy 6-4, 6-7(1), 4-6 despite taking the first set. This was Ramkumar’s 21st attempt to qualify for the singles main draw of a Grand Slam since 2014. He is yet to play a singles main draw match but made his Grand Slam debut in mixed doubles at Wimbledon, where he also lost a tight battle in the last round of singles qualifying.

Prajnesh Guneswaran is the only Indian left in the men’s singles qualifiers. The left-hander is up against Canadian Brayden Schnur later on Wednesday.