Milos Raonic was eliminated from the U.S. Open by Japan's Kei Nishikori in five sets early Tuesday.
The 10th-seeded Nishikori prevailed 4-6, 7-6 (4), 6-7 (6), 7-5, 6-4 to advance to the quarter-finals after a match that had both players straining to find extra reserves of energy at the end.
The match, which started just after 10 p.m. ET on Monday, ended at 2:26 a.m. ET on Tuesday morning, equalling the finishing time of a 1993 encounter between Swedes Mats Wilander and Mikael Pernfors and a 2012 match between Philipp Kohlschreiber and John Isner. At four hours 19 minutes, it's the longest match at this year's U.S. Open.
Asked if he was impressed by that record, Raonic said, "Not in the slightest bit."
With Raonic's defeat, there are no Canadians remaining in the event, as Eugenie Bouchard of Westmount, Que. was beaten in straight sets by Ekaterina Makarova in her fourth round match on Monday.
Nishikori will face third-seeded Stan Wawrinka of Switzerland in the quarter-finals.
Raonic was not happy with the schedule makers, who had him play the first match of the day in the third round and then put him on last two days later.
"It's a little weird, that aspect of scheduling, but the atmosphere and all that was fun," he said. "It was fun how many people stuck around."
Fifth-seeded Raonic found himself in a battle with Nishikori, whose service returns and baseline play had the towering Canadian on his heels for much of the late night match.
After a rare tiebreak loss in the second set, Raonic staved off eight break points in the third. It was his seventh tiebreaker win of the tournament, the most since Younes El Ayanoui in 2003.
"I wish I could have been more efficient in many aspects, like my serves," said Raonic, who was done in by 72 unforced errors despite his 35 aces. "I was losing my serve too many times, especially at the beginning of the match, but I kept fighting and that's all I can ask.
"Then I felt he got a little over me and I was playing to stay alive."
Raonic is 24-10 in tiebreakers for the year, including 16-2 in the hardcourt season.
Wawrinka defeated Tommy Robredo of Spain in four sets on Monday.