Tim Henman produced a battling display but it was not enough to defeat Russian second seed Dmitry Tursunov in round two of the Nottingham Open.
Henman has now lost five of his six matches against Tursunov
Henman fought back from 4-1 down to take the first set into a tie-break only to lose the opener after surrendering three set points.
The Briton recovered to break twice in the second set to level the match.
Tursunov rallied in the decider and sealed a 7-6 (9-7) 3-6 6-2 victory with another superb winner.
Henman has now lost five of his six meetings with Tursunov, three of which were in Grand Slams - at Wimbledon in 2005 and at last year's Australian and French Opens.
Despite the defeat Henman, who has slipped to 78 in the world rankings, insisted he was pleased with his performance.
"I played some good tennis," he said. "In those types of conditions it is so tough to play, you look at the style of the match and Tursunov is just dominating, that is what he can do.
"He is so powerful and you feel like you are just having to react so much, but I feel I did great to get back in the first set and had chances in the tie-break.
"Certainly I would have liked to have taken one of those and perhaps it could have been a different story after that."
Henman had reached round two after claiming only his second tour win this year against Michael Russell in the opening round and he was happy to have had more match practice ahead of Wimbledon next week.
"It's been good for me. More time on the match court is definitely what I have been looking for," he said.
"I would like to have gone further obviously but I have broken a bad run by getting a win under my belt and now I have to take it a step further at Wimbledon."
Meanwhile top seed Richard Gasquet kept his bid for a third straight Nottingham title on track with a comprehensive 6-4 6-0 win over Jan Vacek.
Jamie Murray and Eric Butorac booked their place in the doubles semi-finals with a 6-3 3-6 10-2 victory over Agustin Calleri and Nicolas Lapentti.
Murray and Butorac gained the initiative with a break early in the opening set and, although Calleri and Lapentti fought back in the second, the third seeds had little trouble in winning the champions tie-break.
They were joined in the semi-finals by British duo Josh Goodall and Ross Hutchins, who reached their first ATP doubles semi-final with a nail-biting win over Frenchmen Arnaud Clement and Sebastien Grosjean.
The British wild cards came from a set down to win 2-6, 7-5 17-15.
They will now meet Jonathan Erlich and Andy Ram, the defending doubles champions from Israel.