British number two Cameron Norrie is out of the Canadian Open after a surprise second-round defeat by world number 99 Aleksandar Vukic.
The 29-year-old suffered a 6-3 6-7 (2-7) 6-3 loss to the Australian.
Norrie, now ranked 39 after his run to the Wimbledon quarter-finals in early July, last won a singles title in 2023.
While he registered some good victories during the grass court season, he has so far failed to carry that momentum on to the hard courts, quickly finding himself 3-0 down in the opening set against Vukic, 29.
Norrie appeared to be struggling with illness and had his blood pressure checked midway through the second set, but battled through to level the match.
However, a failure to take advantage of any of his three break points in the rain-interrupted deciding set ultimately cost him against his unseeded opponent.
In the women’s event in Montreal, world number three Iga Swiatek won her first match since lifting the Wimbledon title, breaking Chinese qualifier Guo Hanyu’s serve six times on her way to a 6-3 6-1 success.
Four-time Grand Slam champion Naomi Osaka saved successive match points to overcome 13th seed Liudmila Samsonova 4-6 7-6 (8-6) 6-3.
The 27-year-old survived break points in the 10th game of the second set, before coming back from a 5-2 deficit in the tie-break.
Japan’s Osaka, the world number 49, recorded her first success against a top-20 player since beating Karolina Muchova at the Australian Open in January.
Now working with Tomasz Wiktorowski after announcing on Monday she had split with coach Patrick Mouratoglou, Osaka broke Samsonova twice in the deciding set to clinch victory.
After ending a four-match losing streak in three-set encounters, she will face Jelena Ostapenko in the third round after the Latvian beat Mexico’s Renata Zarazua 6-2 4-6 6-2.
British number one Emma Raducanu is in action on Wednesday against Peyton Stearns.
