Denis Shapovalov's losing slump has continued with a 7-6 (9-7) 7-6 (8-6) defeat to Luxembourg's Gilles Muller in the first round at Queen's Club in London.
It is Shapovalov's second consecutive first-round loss after exiting the Stuttgart Open at the opening hurdle last week after losing to Indian qualifier Prajnesh Gunneswaran.
However, this will be tougher for Canada's Shapovalov to take as he was evenly matched with Muller on serve throughout, only for the world No.46 to find the edge in both tiebreaks.
Meanwhile, Switzerland's Stan Wawrinka eased through as he swept aside Briton Cameron Norrie 6-2 6-3 in less than an hour.
Wawrinka, who has previously won three grand slam titles, enjoyed his success on the grass and felt content with his efforts.
The 33-year-old believes that the knee injury that almost ended his career at Wimbledon last year is now behind him.
"I think, in general, it's been improving week after week and I feel the difference on the court," Wawrinka said.
"I served well and it's never easy playing first round on the grass. Today was a great day and I'm happy to be back winning."
Wawrinka earned the first break at 3-1 before a backhand dropped inside the line to seal the first set inside 27 minutes.
Norrie wilted under the relentless efforts from the Swiss as Wawrinka served solidly to sail into round two, where he will meet American Sam Querrey.
Shapovalov, ranked No.23 in the world, saved a break point at 5-5 before ultimately heading into a first set tiebreak with the big-serving Muller.
A handful of errors from Shapovalov allowed Muller to keep level to 7-7 in the tiebreak until the 19-year-old Canadian's premature strike caught the top of the net, resulting in him falling behind.
Undeterred from losing the first set, Shapovalov released a rapid backhand winner to hold his opening service game in the second set.
Neither player could break serve and were again pegged in the tiebreak until Muller found the winning stroke as the clock went past 100 minutes.
Muller will face Marin Cilic in the next round after last year's runner-up beat Fernando Verdasco in straight sets.
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