Novak Djokovic lost to Jan-Lennard Struff in the Swiss Indoors round of 16 on Thursday. The 39-year-old Serb fell 6-7, 7-5, 7-6 as Struff fired 27 aces. Meanwhile, top-seeded Ben Shelton got shocked by Swiss wild card Jerome Kym. Kym won 6-3, 6-7, 7-6 in a tough night session match.
Djokovic came to Basel for the first time in 15 years, where he won one of his 102 titles against Roger Federer in the 2009 final.
Novak Djokovic won't be matching Roger Federer's 103 career titles at the Swiss icon's hometown tournament this week as he endured a tough loss on Thursday at the Swiss Indoors, going down 6-7 (4), 7-5, 7-6 (5) to 47th-ranked Jan-Lennard Struff.
Top-seeded Ben Shelton won't be winning his eighth career title in Basel. He lost to 222nd-ranked Swiss wild card Jerome Kym 6-3, 6-7 (4), 7-6 (1) in a shocking night session.
Djokovic lost the round of 16 tie when his 36-year-old German opponent fired his 27th ace down the middle, which the 39-year-old Serb could not reach. Djokovic had saved a second match point with an ace of his own.
The record 24-time Grand Slam singles champion won his 102nd tour event this month in Beijing. Only Jimmy Connors, with 109 career titles, has more than Federer's 103.
Djokovic came to Basel for the first time in 15 years, where he won one of his 102 titles against Federer in the 2009 final. The next year, Federer won their rematch in Basel, where he grew up, was once a ball boy, and lifted the trophy a record 10 times.
U.S. Open finalist Shelton now has a hat-trick of losses this season to opponents with rankings in the triple digits. Kym's 222 ranking follows No. 140 Otto Virtanen at Wimbledon and No. 117 Nikoloz Basilashvili in Rome.
Shelton also lost this season to seven more opponents ranked between 87 and 56, while winning four titles on three different surfaces.
The No. 4-ranked American twice salvaged precarious positions Thursday, when two points from defeat serving at 5-6 in the second set and trailing by two breaks at 5-2 down in the decider after midnight.
The 23-year-old Kym, a tall right-hander who typically only plays in main draws in his home country, Switzerland, raised his game in the final tiebreak. He clinched it with an impressive backhand passing shot played at full stretch while running toward the net.
Kym next faces Jiri Lehecka on Friday after the eighth-seeded Czech won 7-5, 6-4 on Daniel Altmaier.
Earlier, second-seeded Arthur Fils dropped the first set in a tight 4-6, 6-3, 7-6 (5) win over No. 34 Alex Michelsen of the United States.
In the quarterfinals Fils will face another American, sixth-seeded Taylor Fritz, who eased to a 6-4, 6-3 win over Denis Shapovalov.