MUNICH — Former champion Philipp Kohlschreiber upset second-seeded Karen Khachanov 7-6 (6), 6-4 Thursday to reach the quarterfinals of the Munich Open.
Kohlschreiber, who won the tournament in 2007, 2012 and 2016, had to save a set point in the tiebreaker then earned the decisive break for a 5-4 lead in the second before serving out the match. The loss extended a recent slump for Khachanov, who has not won a single set since the Indian Wells tournament in March. He also lost his opening matches at Miami, Monte Carlo and Barcelona since then.
Kohlschreiber will next face Matteo Berrettini of Italy, who beat unseeded American Denis Kudla 7-5, 6-3. Kudla, who is ranked 82nd, had upset the fifth-seeded Kyle Edmund on Tuesday.
Also Thursday, the fourth-seeded Roberto Bautista Agut defeated German wild card Rudolf Molleker 6-4, 6-2 to set up a meeting with Guido Pella, who ousted Taro Daniel of Japan 6-1, 6-7 (7), 6-3.
ASTANA, Kazakhstan — Carlos Alcaraz’s first match as the No. 1-ranked player ended with a straight-set loss to David Goffin at the Astana Open.
The 19-year-old Spaniard lost 7-5, 6-3 in his first tour match since winning the U.S. Open and capturing the No. 1 ranking.
“David was playing really, really well. To come back to competition is never easy,” Alcaraz said. “It’s really tough for me, for my confidence.”
Alcaraz came from 5-2 down to level the first set at 5-5, only to be broken again by his Belgian opponent.
“When you play against the World No. 1 on a big stage, big crowd, the fire inside gives you so much power to play your best tennis because you don’t have any choice,” Goffin said. “You have to fight and give your best and that was the case today.”
Second-seeded Daniil Medvedev and No. 3-seeded Stefanos Tsitsipas both avoided similar upsets. Medvedev beat Albert Ramos-Vinolas of Spain 6-3, 6-1 and Tsitsipas ousted Kazakhstan’s Mikhail Kukushkin 6-3. 6-4.
OSTRAVA, Czech Republic — Fifth-seeded Daria Kasatkina defeated 2021 U.S. Open champion Emma Raducanu 7-5, 6-4 to advance to the second round of the Agel Open.
Kasatkina was playing her first match since losing in the first round of the U.S. Open and will next face Ekaterina Alexandrova.
Sixth-seeded Belinda Bencic of Switzerland rallied to eliminate former top-five player Eugenie Bouchard of Canada 6-7 (7), 6-1, while Aliaksandra Sasnovich upset eighth-seeded Jelena Ostapenko 6-2, 6-2.
American qualifiers Alycia Parks and Catherine McNally both advanced. Parks upset Czech Karolina Pliskova 6-0, 7-6 (3) and McNally eased past Anna Blinkova 6-1, 6-2 at the indoor hardcourt event in the Czech eastern city of Ostrava.