Cameron Norrie’s miserable run continued as he came up short in an arduous three-set battle against big-serving Canadian Milos Raonic in the first round at Queen’s Club.

The 28-year-old, who lost his British number one spot to Jack Draper over the weekend, had two match points in a marathon third-set tie-break but lost 7-6 (6) 3-6 7-6 (9) in two hours and 15 minutes.

Norrie has endured a difficult season – and a rotten few weeks – having lost eight of his last 14 matches including a first-round exit at the French Open and a defeat at Nottingham last week by world number 773 Jack Pinnington Jones.

Former world number three Raonic may have slipped to 186 in the rankings after three years of injury problems, but he is still in possession of one of the game’s most potent serves.

Norrie endured a set of the 33-year-old’s 140mph missiles whizzing past him before pouncing in the tie-break, saving a set point before edging ahead.

When Raonic immediately broke the Norrie serve, the second set was only going to go one way.

Cameron Norrie looks frustratedNorrie (pictured) lost his British number one spot to Jack Draper over the weekend (Mike Egerton/PA)

In the third-set tie-break, Norrie failed to convert two match points and Raonic – who hit a three-set ATP Tour match record 47 aces in total – put away his first to condemn the 2021 runner-up to an early exit.

Summer had broken out on the posh lawns of West Kensington, but the first day of the cinch Championships was not without its controversy.

Seventh seed Holger Rune branded the court “terrible” after he kept slipping on the damp grass as he tumbled to a three-set defeat to Australia’s Jordan Thompson.

“This court is so slippy,” the young Dane moaned to umpire James Keothavong.

“Terrible court, what is this? I can’t stand on the court. It’s too wet. Call the supervisor. I fell three times. It’s too wet. You think I’m falling on purpose?”

American Frances Tiafoe also came a cropper, having to retire from his match against Australian qualifier Rinky Hijikata after a nasty fall.

Bulgarian veteran Grigor Dimitrov, the 2014 champion and current world number 10, cruised past France’s Adrian Mannarino 6-1 6-2.