Kyle Edmund crashed out of the Aegon Championships at Queen’s after losing 6-7 6-4 4-6 to Canadian qualifier Denis Shapovalov in the first round.
Shapovalov, 18, prevailed against British No 2 Edmund having been disqualified in their last encounter in February – a Davis Cup tie which ended with the Canadian smashing a ball into the face of umpire Arnaud Gabas.
The Queen’s first-round match was a tight affair, and a first break opportunity for Edmund also brought up set point at 5-4 in the first, 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 duo 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.
Shapovalov will now play Tomas Berdych in the second round after the Czech proved too strong for Steve Darcis, winning 7-5 6-3 on Court 1.
Elsewhere, Nick Kyrgios’ hopes of being fit for Wimbledon were dealt a blow after he retired hurt following a nasty fall against American opponent Donald Young.
The 22-year-old required lengthy treatment after slipping with the score at 4-4, and though the Australian opted to carry on, he withdrew after losing the first-set tie-break.
The world number 20 remained optimistic about his Wimbledon chances, while he joked that he would spend the rest of the week at the pub following his early withdrawal.
“I mean I’d play Wimbledon if I was injured pretty bad anyway,” Kyrgios said. “I’m here anyway. I don’t really have time to go home or anything. Yeah, I will be playing for sure.”
Kyrgios was then asked what he would be doing now instead this week, and he replied, smiling, “Dog and Fox”, referring to a pub located close to Wimbledon.
His unexpected exit means Young goes through to face either Viktor Troicki or Janko Tipsarevic in the second round.
Earlier in the day, fifth seed Jo-Wilfried Tsonga beat fellow Frenchman Adrian Mannarino 6-2 6-2, while Grigor Dimitrov powered past Ryan Harrison 6-3 6-1.
Meanwhile, the Gerry Weber Open kicked off in Halle on Monday – with Richard Gasquet prevailing 3-6 6-4 6-3 in a thrilling tie against fellow Frenchman Gael Monfils.
Earlier, Philipp Kohlschreiber battled past Joao Sousa 3-6 6-4 6-4 before Andrey Rublev beat Albert Ramos-Vinolas 6-7(1) 7-5 6-4. Dustin Brown then won an entertaining encounter against Vasek Pospisil 6-1 6-7(3) 7-6(4).
18-time Grand Slam champion Roger Federer will be in first-round action on Tuesday in Halle, live on Sky Sports.