Tim Henman crashed out of the US Open in five sets against Belgium's Xavier Malisse, 6-7 6-3 7-5 4-6 6-4.
After both men dropped serve in the opening set, Henman squandered three set points before taking the tie-break 8-6.
But Malisse - trained by Henman's former coach David Felgate - began to take control as Henman's serve faltered to clinch the second set 6-3.
Henman again produced far too many double faults for comfort as the Belgian won the third set 7-5 to take control of the match.
However, the British number one did not buckle under the pressure and broke his opponent in the 10th game of set three to win 6-4 and square the match.
Henman found himself 3-0 up in the deciding set, but could not push his advantage home as Malisse fought back to lead 5-4 and serve for the match.