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.
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.
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.