British No 2 Cameron Norrie crashed out of the Canadian Open following a three-set defeat to Aleksandar Vukic.
The 29-year-old overcame a one-set deficit and a medical timeout to force a decider against the Australian world No 99 in the second-round match in Toronto.
But Norrie, who received a first-round bye, was unable to complete the comeback as his US Open preparations were dealt a blow by a 6-3 6-7 (2) 6-3 defeat in just over two hours.
Despite saving four break points, the world No 39 dropped his opening service game, paving the way for Vukic to wrap up the first set in 33 minutes.
That proved to be the only break of serve across the opening two sets, with Wimbledon quarter-finalist Norrie ultimately levelling courtesy of a tie-break after requiring on-court treatment while leading 6-5 in the second set.
Norrie was then unable to capitalise on two break points in game five of the final set, a pivotal moment compounded by him immediately failing to hold.
Vukic was one game from victory when a rain delay prolonged the match before returning to finish the job and set up a last-32 meeting with either American seventh seed Frances Tiafoe or Japanese qualifier Yosuke Watanuki.
Osaka saves three match points to beat Samsonova
Please use Chrome browser for a more accessible video player
Highlights of Liudmila Samsonova against Naomi Osaka at the National Bank Open in Montreal
Japan’s Naomi Osaka saved three match points to beat Liudmila Samsonova 4-6 7-6 (6) 6-3 in the second round of the Canadian Open on Wednesday.
Samsonova forced three match points at 5-4 up – and on serve – in the second set, but the four-time Grand Slam champion managed to save each one to take the match to a decider in Montreal.
From there, Osaka continued to gain momentum and showed great determination as she registered two breaks in Samsanova’s first three service games in the decider.
Osaka will face Latvia’s Jeļena Ostapenko in the third round.
Watch the ATP and WTA Tours, as well as the US Open in New York, live on Sky Sports in 2025 or stream with NOW and the Sky Sports app, giving Sky Sports customers access to over 50 per cent more live sport this year at no extra cost. Find out more here.
AloJapan.com