Milos Raonic came up short in the longest match of his professional career.
Raonic missed out on tennis history Saturday, failing to become the first Canadian man to reach the fourth round of the French Open as he lost to Argentina's Juan Monaco 6-7 (5), 6-3, 6-7 (5), 6-3, 6-4.
It was also the first time the 22-year-old from Thornhill, Ont., played a five-set match on the ATP Tour.
"I wish I could have played better," said Raonic, who will start his grass campaign in just over a week at Halle, Germany. "I really didn't do a lot of things well so I was just trying to make the most of it and I was able to have my opportunities — to have my chances."
Raonic is the fifth Canadian to get this far in Paris, after Robert Murray in 1936, Robert Bedard and Lorne Main in 1954, and Greg Rusedski in 1994.
Raonic, the tournament's 19th seed, duelled Monaco for four hours 33 minutes before going down as his forehand hit the net to end the match. Raonic saved two match points late in the fifth set to prolong his time on the court.
"I hung in but I wasn't winning many of the rallies — I wasn't hitting my forehand well and I was making a lot of mistakes with it," said Raonic. "My backhand had fewer mistakes but it wasn't doing anything."
Earlier, Toronto's Daniel Nestor and partner Max Mirnyi of Belarus defeated Australians Paul Hanley and Jordan Kerr 6-1, 7-6 (0) in the second round of the men's doubles tournament.
Raonic finished with 26 aces against Monaco in the pair's first meeting. He managed a massive 73 winners counter-balanced by 88 unforced errors and was unable to convert on any of his eight break points.
"He's a very good clay-court player — a top-10 clay-courter," Raonic said.
Raonic has a 24-8 record in 2012 with titles at Chennai and San Jose this season. He has a career 2-2 record at Roland Garros.
"It was disappointing knowing I could do better — but in the end it's a good thing," said the Canadian. "It's a good thing to push it that much just through mentally and competing rather through good play."
Monaco took control in the final set after Raonic saved five break points in the opening game of the final chapter. But Raonic then lost serve in the third game on a double fault and was never able to catch up.
Raonic and Monaco played level through most of the opening set, which proceeded at a leisurely pace. When the set reached a tiebreaker, the 21-year-old Canadian took a 4-2 lead, only to find himself level 4-4. Raonic produced a chip volley winner for two set points and wrapped up the opener in 58 minutes as he fired a big serve, then wrong-footed Monaco on a return.
The duel continued in the second set, with Monaco breaking for 4-2. Raonic struggled to close the gap and saved five set points in the ninth game and put the Argentine under pressure with a break point.
Monaco salvaged it and finally claimed the set as Raonic netted a cross-court shot, 3-6.
The third set tightened as Raonic missed on three set point chances while leading 5-4, netting his third as Monaco held for 5-all. Raonic took a 4-1 lead in the ensuing tiebreak, but was caught by his opponent as the pair went to 5-5 before the Canadian produced a service winner for a two-sets-to-one lead.
Monaco earned a break for 2-0 in the fourth, which proved to be enough to take the match into a fifth set. Raonic saved a set point in the eighth game but found himself all square at two sets each a game later as Monaco converted on a second opportunity.