Canadians Milos Raonic and Eugenie Bouchard both advanced to the fourth round of the French Open Friday in Paris.

Both survived some tense moments before earning history-making wins.

Raonic, the men's No. 8 seed from Thornhill, Ont., needed more than three hours to overcome Frenchman Gilles Simon 4-6, 6-3, 2-6, 6-2, 7-5 and become the first Canadian man into the fourth round at Roland Garros.

Earlier, Bouchard recovered from early breaks in both sets as she beat Swede Johanna Larsson 7-5, 6-4.

Raonic fired 19 aces but rode a roller coaster as he was broken while serving for victory.

But the 23-year-old then broke Simon to go up 6-5, and earned the victory in the ensuing game when Simon hit a long return on match point.

Raonic advanced with 60 winners and six of 12 break points converted, but also committed 74 unforced errors.

"It was just incredible to play a tough opponent like Gilles, I'm very content with this win," said Raonic. "We were on court a long time and I'm a bit tired. When I was broken serving for it, I just told myself I had to break back and go from there. I stayed calm.

"This is my first fourth round here and it's a very important win for me. It's also my first in a big showcourt like this at a Grand Slam. It's all super for me, I want to continue."

The 18th-seeded Bouchard, an Australian Open semifinalist earlier this year, showed fighting spirit in winning her 84-minute match with the 99th-ranked Larsson in the pair's first meeting.

"I started a little slow, I was just a bit rusty on the court," said Bouchard. "But I didn't worry or anything on the court.

"I still had a lot of confidence in myself just to get my groove, and after a few games I started playing much better and really got into the match. The whole match I felt very comfortable and confident.

"She plays well, and especially on clay. So it was it was definitely tough."

She is the first Canadian woman since Aleksandra Wozniak to get this far in Paris.

Bouchard finished with 27 winners and 30 unforced errors, breaking on six of 11 chances while losing serve four times.

Montreal's Bouchard lost the opening game but recovered nicely to take a 5-3 first-set lead. She got into trouble as Lasson levelled for 5-all but claimed the set with a break for 7-5 on her third set point.

The Canadian lost serve in the third game of the second, breaking back in the fourth to tie the set at 2.

Bouchard earned a 4-2 lead as she move on to victory, with Larsson donating a double-fault for a second match point before volleying a forehand return low into the net.

Next up for Bouchard is German eighth seed Angelique Kerber, who beat Daniela Hantuchova 7-5, 6-3.

"I'm just trying to enjoy every moment, believe in myself, and I know that I have a chance," Bouchard said. "Every time I walk on the court I have a chance to win.

"It's going to be important to try to start strong in my next match, no matter what."

In mixed doubles, Toronto's Daniel Nestor and French partner Kristina Mladenovic opened with a 6-7 (1), 6-4 defeat of Max Mirnyi of Belarus — a former Nestor men's doubles partner — and Taiwan's KC Chan.

Djokovic, Federer move on

In what seemed like a flash, and in what surely felt like a flash of pain for his opponent, Roger Federer went from vulnerable to commanding.

It was that quick.

Federer lost a second-set tiebreaker to Dmitry Tursunov, and that surely did not bode well for the 17-time Grand Slam champion. Then Tursunov felt a split second of discomfort in his left hip.

And that was it.

Federer was back on track at the French Open, on his way to a 7-5, 6-7 (7), 6-2, 6-4 victory and into the second week of a major tournament yet again.

"Everything that was out of his control, like moving defence, that's when it got difficult," said Federer, who advanced to the fourth round at Roland Garros for the 10th straight year. "Clearly, on the clay, it's difficult to hit three great shots in a row. So I tried to extend the rallies, but serve nice and stay aggressive throughout. And I think that was a bit too much for his hip, or whatever it was."

It was something of an escape for Federer, who lost a set for the first time at this year's tournament. Then again, Novak Djokovic also lost a set Friday before advancing with a 6-3, 6-2, 6-7 (2), 6-4 win over 25th-seeded Marin Cilic.

With eight-time champion Rafael Nadal and 2013 finalist David Ferrer perfect through their opening two matches, the pressure is on the others to keep their level high.

"It wasn't easy because once you start being passive, you lose kind of the confidence to step in," Djokovic said of his win. "That's what happened maybe in the end of the third and a little bit of the fourth."

More upsets on women's side

Of course, that's nothing compared to the women's tournament, where third-seeded Agnieszka Radwanska followed defending champion Serena Williams and Li Na out of the tournament.

That leaves Simona Halep, who plays Saturday, as the highest-seeded player in the draw at No. 4. It also leaves 2012 French Open champion Maria Sharapova as the favourite after her 6-0, 6-0 rout Friday.

The woman who beat Williams, Garbine Muguruza of Spain, also advanced to the fourth round.

Federer and Djokovic, though, were expected to win, and they did. Tursunov, with an 0-4 record against Federer heading into the match, wasn't, and he didn't.

"Overall, the first two sets ... I felt that it was a fairly even battle out there," said Tursunov, who was broken only once in the first two sets. "It's hard for me to predict, but definitely playing on one leg is not going to make things easier. Tough luck for me, but hopefully I'll get him somewhere else."

It's still not completely clear what happened to the 31st-seeded Tursunov, but it most certainly led to a bit of a meltdown a few minutes later.

"It was right after the changeover of the second set," he said. "We sat down and then got up and then he was serving, and then right after the first serve was kind of like, 'Something is not right."'

Federer broke Tursunov in that opening game, and led 2-1 at the first changeover. Tursunov called for a trainer, and started to lose his cool. He screamed at the chair umpire, yelling "start using your brain," while angrily mixing his personal purple drink. A medical trainer came out and chatted with the Russian while he continued fiddling with the plastic bottle and a funnel.

Finally, Tursunov left the court and headed for a training room in the bowels of Court Philippe Chatrier. Meanwhile, out on the red clay of the main stadium, Federer was practicing his serves, drawing some boisterous shouts of "Ole" from the waiting crowd.

When Tursunov finally returned, the match was in Federer's hands.

"Where I felt it the most was that he struggled to return the serve, the reaction, left and right was maybe missing a little bit," Federer said. "But in terms of playing aggressive tennis, that he was able to do normally, in my opinion."

The problem for Tursunov, however, was that aggressive tennis wasn't enough on this day.

"I like how I'm playing against him. Hoping to improve," Tursunov said, again thinking ahead to a possible sixth meeting. "Hoping to give him more difficulties for the next couple years, hopefully."

With files from The Associated Press