Andy Murray fought for nearly three and a half hours with a Czech teenager but was unable to hold off the youngster, taking a 7-6 (6), 6-7(3), 7-6 (4) loss to Jakub Mensik on Wednesday in Doha.
The 36-year-old Scot came close to winning his second in a row after cracking a six-match loss streak 24 hours earlier at the ATP event.
But Mensik held his nerve after twice failing to serve out the win, leading 5-2 and 5-4 in the deciding set.
The final set went to a tiebreaker, with the 116th-ranked outsider moving into his first career Tour quarter-final as Murray’s return on a first match point in the tiebreaker hit the bottom of the net.
“I’m speechless,I don’t know what to say. I know lots of fans wanted Andy to win.
“I’m just happy I got through a tough match, He’s an unbelievable player – I used to watch him winning Wimbledon when I was young,” said the player born in 2005 when Murray was already a professional.
Mensik recovered while trailing in the first of the three tiebreaks and also started 0-2 in the final decider
“The first set was tough, with windy conditions,” he said. “The tiebreak was not so high quality and I got a bit lucky in the end.
“Even when I was up in the third set, I knew he would not give me any points, I just tried to stay calm and focused.”
Murray missed out on his 500th Tour-level win on hard courts; the Scot already had eight ATP wins before his opponent was born.