British number two Cameron Norrie suffered potentially one of the most crushing defeats of his career as he lost to Milos Raonic in three sets in the first round at Queen's.
The former Wimbledon semi-finalist has struggled for form all season and was recently dethroned at the top of the British tennis rankings by Jack Draper owing to the 22-year-old's triumph at the Stuttgart Open.
Norrie - who was surprisingly beaten by Jack Pinnington Jones in last week's Nottingham Challenger event - sought to get back on track against Raonic, but despite taking the first set, he collapsed and lost a gripping final-set tie-breaker as his Canadian foe prevailed 6-7[6] 6-3 7-6[9].
Raonic - who was runner-up to Andy Murray at the 2016 Wimbledon Championships - etched his name into the record books in the process, coming up with an outrageous 47 aces over the course of the two-hour and 15-minute battle.
The 33-year-old's serving masterclass saw him set a new all-time record for the most aces ever registered in a three-set match, surpassing the previous holder Ivo Karlovic, who hit 45 in a Halle quarter-final against Tomas Berdych in 2015.
Norrie fired a respectable 12 aces of his own, but his feats paled in comparison to history-maker Raonic, who held to love in the 10th game with a quartet of perfect serves, only to lose the tie-breaker on an unforced error.
However, the Canadian responded emphatically with an immediate break in set two before saving a break-back point and holding for 3-0 with three successive aces, and Norrie had no answer to his opponent's serving clinic.
There was not a single break to be had in the 12 games of the third set, leaving the contest to be decided on a nerve-jangling tie-breaker, where both men let a few match points slip through their grasp.
Norrie - who fought back from 5-2 down in the closing act - let two pass him by while Raonic missed two of his own, but after bringing up his third with ace number 47, the Canadian finally got over the line after a gargantuan effort.
As well as improving his record over Norrie to 3-0, Raonic - who entered this year's Queen's Club Championships via a protected ranking - earned a second-round date with either Taro Daniel or Taylor Fritz.
Which Brits are in action on Tuesday? Are Murray, Raducanu playing?
While one British hope is already out, four more home favourites take to the Queen's courts on Tuesday, including five-time singles winner Andy Murray, who faces Australian qualifier Alexei Popyrin.
Meanwhile, new national number one Draper faces Mariano Navone, Daniel Evans is up against Brandon Nakashima, and Billy Harris faces a tough examination against Tomas Martin Etcheverry.
Over at the Birmingham Open, Katie Boulter - fresh from defending her Nottingham Open title - takes on Anhelina Kalinina, while Heather Watson and Harriet Dart tackle Marie Bouzkova and Moyuka Uchijima respectively.
Amelia Rajecki is also up against Diana Shnaider, but Emma Raducanu - who reached the Nottingham semi-finals - is not involved in the draw. body check tags ::
