Cameron Norrie will go into Wimbledon with just one singles grass-court win to his name after losing to Maxime Cressy in the Eastbourne last eight
The top seed and British number one was edged out 7-5 7-5 by American Cressy.
Fellow Briton Ryan Peniston reached a second ATP quarter-final in a week as he beat Pedro Martinez 7-6 (10-8) 3-6 6-3.
Peniston will play a second match later on Thursday against Jack Draper, while Harriet Dart takes on Petra Kvitova.
Peniston and Spain’s Martinez were tied at a set apiece when bad light held up play on Wednesday.
The two exchanged breaks when play resumed, before Peniston found the decisive break and served out victory.
He will face compatriot Draper as he bids for a first ATP semi-final.
Norrie, who has never gone beyond the third round at Wimbledon, was disappointed to let the first set slip after a tight contest.
The Briton led by a break before Cressy hit back, with his serve-and-volley technique proving effective.
Norrie served to take the set into a tie-break but a long pass brought up set point, before an unfortunate bobble off the net cord handed Cressy the opener.
World number 12 Norrie had the first break-point opportunity of the second set but it was saved by a Cressy volley and the Briton’s serve began to falter.
He saved three match points in a row after going 0-40 down on serve but he was unable to stop Cressy converting the fourth.
Wimbledon begins on Monday.