Kyle Edmund has crashed out of Queen’s after a 6-7 (4-7) 6-4 4-6 defeat to world No. 193 Denis Shapovalov.
Grass is not the British No. 2’s favoured surface and he was taken out by the talented 18-year-old at the Aegon Championships.
Edmund had just enjoyed another good run at a Grand Slam, reaching the third round at the French Open before losing to Kevin Anderson, but he is yet to win a match in the Wimbledon main draw.
And his latest loss on grass will not have filled him with much confidence heading to the All England Club.
The pair’s first meeting ended in rather unusual circumstances as the young Canadian thumped a ball in anger, which unfortunately smacked umpire Arnaud Gabas in the face and saw him disqualified from their Davis Cup tie.
Shapovalov has since risen 41 places in the rankings to world No. 193 and the 18-year-old looks a talented prospect on grass.
His big swinging left-handed serve kept Edmund largely at bay in the opener as he took the first set on a tiebreak.
The Brit did, however, hit straight back, breaking early in the second before levelling the match up, looking steady on his own serve throughout.
With more good work on their serves, the final set followed a similar pattern, with Shapovalov getting the break at the death.
He will now face Tomas Berdych in the second round, after the Czech beat Belgium’s Steve Darcis in straight sets.
The 7th seed won 7-5 6-3 to fellow seeds Grigor Dimitrov and Jo-Wilfried Tsonga in the next stage, although 9th seed Nick Kyrgios was forced to withdraw with a hip injury.