James Blake's career ended in a fifth-set tiebreaker at the U.S. Open after he won the first two sets.
The 33-year-old American lost 6-7 (2), 3-6, 6-4, 7-6 (2), 7-6 (2) in the first round to Ivo Karlovic just after midnight Thursday morning.
Blake announced Monday that this would be his last tournament.
He rallied from down a break in the final set to force the tiebreaker, but couldn't overcome the 6-foot-10 Croat's big serve at the end.
Karlovic closed out the victory in 3 hours, 24 minutes with his 38th ace.
Blake had won 11 straight first-round matches at Flushing Meadows since losing in his debut in 1999. He has been ranked as high as No. 4 in the world in his career and reached three Grand Slam quarterfinals.