Britain’s Dan Evans is out of the Japan Open after missing six match points in his second-round match with Serbia’s Miomir Kecmanovic.
The British number two came back from a set down and then recovered from being 4-2 down in the deciding set to leave himself serving for the match at 5-4.
The 32-year-old is ranked 33 in the world, eight places above Kecmanovic.
Meanwhile, Nick Kyrgios came back from a set down to defeat Poland’s Kamil Majchrzak.
The Australian won 3-6 6-2 6-2 to reach Friday’s quarter-finals.
Evans, who went out of the Korea Open to Yoshihito Nishioka in September, was 40-0 up and had three further match points in the same game but was unable to take any of them.
The Serb then missed a match point of his own at 6-5, before winning the final four points of the tie-break to take a 6-3 3-6 7-6 (7-4) win.
Evans also went out of the doubles in the quarter-final alongside Australian partner John Peers, losing 2-6 7-6 (7-5) 10-6 to Mackenzie McDonald, of the USA, and Brazilian Marcelo Melo.
Djokovic and Medvedev through in Kazakhstan
At the Astana Open in Kazakhstan, Novak Djokovic and Daniil Medvedev are through to the quarter-finals after straight-set victories.
Djokovic, seeded fourth, defeated the Netherlands’ Botic van de Zandschulp 6-3 6-1 to set up a last-eight meeting with Karen Khachanov, who beat ninth seed Marin Cilic.
Khachanov’s Russian compatriot and second seed Medvedev beat Finland’s Emil Ruusuvuori 6-3 6-2 and will next face Roberto Bautista Agut.
Also through to the quarter-finals is Poland’s Hubert Hurkacz, after the seventh seed beat home favourite Alexander Bublik 6-4 6-4. He will play Greek third seed Stefanos Tsitsipas in the next round.