NEW YORK -- Canadian Milos Raonic lost to France's Richard Gasquet in five sets on Monday in the fourth round of the U.S. Open.
The pair needed more than four hours 40 minutes to settle the match 6-7 (4), 7-6 (4), 2-6, 7-6 (9), 7-5.
Gasquet advances to play Spain's David Ferrer in the Grand Slam tournament's quarter-final.
Raonic, from Thornhill, Ont., matched his previous best at a Grand Slam.
He'd previously made the fourth round in the Australian Open (2011, 2013) and the U.S. Open (2012).
In other action, Rafael Nadal is undefeated in 19 matches on hard courts this year after coming back to beat 22nd-seeded Philipp Kohlschreiber of Germany 6-7 (4), 6-4, 6-3, 6-1 and return to the U.S. Open quarterfinals.
He will not, however, play Roger Federer next.
The second-seeded Nadal, who counts the 2010 U.S. Open among his 12 Grand Slam titles, beat Kohlschreiber on Monday night in the fourth round.
Their match ended about 2 1/2 hours after Federer was upset in straight sets by 19th-seeded Tommy Robredo, Nadal's quarterfinal opponent. Had Federer won, he and Nadal would have played each other for the 32nd time -- and first at Flushing Meadows.
Against Kohlschreiber, Nadal faced only one break point, and saved it. Nadal has yet to lose a service game in the tournament.
Federer, indeed, looked very little like, well, the Roger Federer who routinely reached the final weekend at Grand Slam tournaments.
In the opening game of his fourth-round match at the U.S. Open, the owner of 17 major titles got passed at the net twice, sailed a backhand long, then missed two forehands to get broken. In the second game, the man who has spent more weeks ranked No. 1 than anyone else dumped a backhand into the net, then shanked two other backhands several feet wide.
No longer the dominant presence he once was, Federer lost in the round of 16 at Flushing Meadows for the first time in a decade, surprisingly beaten 7-6 (3), 6-3, 6-4 by 19th-seeded Tommy Robredo of Spain on Monday night.
"I kind of self-destructed, which is very disappointing," said Federer, who made 43 unforced errors and managed to convert only 2 of 16 break points. "It was a frustrating performance."
Only the latest in a series. This caps a poor-by-his-standards Grand Slam season for Federer, whose record Grand Slam trophy collection includes five at the U.S. Open.
He exited in the semifinals at the Australian Open in January, the quarter-finals at the French Open in early June, and the second round of Wimbledon -- against a player ranked 116th, to boot -- in late June. That ended Federer's record run of reaching at least the quarter-finals at 36 consecutive Grand Slam tournaments.
Now, thanks to Robredo, Federer has a new, unwanted streak: Two consecutive losses before the quarterfinals at majors.
This is the first season since 2002 that Federer did not reach at least one final at any of the four Grand Slam tournaments. That year also marked the last time Federer was ranked lower than he is now at No. 7.
"The story of my life: When I lose, people are shell-shocked to see me play this way," Federer, 32, said.
-- The Associated Press