Cameron Norrie suffered a fourth-consecutive defeat as his poor form continued at the Japan Open.
The British number one was not helped by drawing top seed and defending champion Taylor Fritz in the first round but his 6-4 6-3 loss made it seven defeats in his last eight matches and 11 out of 14 dating back to Wimbledon.
Norrie recovered from an early break of serve in the opening set in Tokyo to pull back to 4-4 only to lose consecutive service games, giving Fritz the advantage he needed.
There was also defeat for Jack Draper but he pushed fourth seed Alex De Minaur all the way in a gruelling clash lasting three hours and five minutes.
Draper, who came through qualifying, won the opening set before De Minaur fought back to take the second on a tie-break.
Draper had the chance to serve out the match when he broke for 5-4 in the deciding set but he began to struggle with cramp and De Minaur hit straight back, eventually sealing a 4-6 7-6 (4) 7-6 (1) victory.
