British number two Kyle Edmund was knocked out in the first round of the Aegon Championships at Queen’s Club by Canadian teenager Denis Shapovalov.
Edmund, who is ranked 146 places higher than Shapovalov at 47th in the world and reached the quarter-finals at Queen's last year, saw his 2017 campaign end in disappointment.
But 18-year-old Shapovalov produced one of the performances of his career to win 7-6 (7-4) 4-6 6-4, and will now go on to face Czech seventh seed Tomas Berdych.
Edmund looked to have the better of the first set as the first break point of the match was also a set point, but Shapovalov battled back to hold serve before going on the win the tie-break 7-4.
Edmund started the second set brilliantly, breaking Shapovalov to love in the first game before holding out to take the match to a decider.
The pair went toe-to-toe in the final set but a collapse in the tenth game brought up three match points for Shapovalov on Edmund's serve.
The first two were saved, but a mishit handed the Canadian victory over the Brit.
Edmund said: “It's my first match on grass after focussing on the clay. I didn't expect to play your best tennis first match and that was certainly the case.
“He's been playing a few matches on the grass, which I think probably helped him.
“He just played aggressively and while it's disappointing. I've plenty of time to prepare for Wimbledon.”
At the Aegon Classic in Birmingham, Heather Watson was beaten by world number five Elina Svitolina.
The British number three played an excellent second set to level the match but one break of serve in the decider proved decisive, with Svitolina going on to win 6-2 5-7 6-3.
Sportsbeat 2017