In the first pair of men’s quarterfinals at the French Open, a former finalist aims to edge closer to a career Grand Slam, while a dangerous underdog looks to continue his surprise run.

Milos Raonic vs. Novak Djokovic

Milos Raonic has navigated his way through a tricky section of the draw to advance to the quarterfinals of a Grand Slam for the first time in his career. His reward? A best-of-five match on an exceptionally slow court against Novak Djokovic.

Djokovic and Raonic most recently met in the semifinals of the Rome Masters just under three weeks ago. The Serbian was the heavy favorite, but he needed three sets and just over three hours to seal the deal. By stretching Djokovic deep into a third set, Raonic demonstrated just how lethal his serve has become and how much his baseline game has improved.

This will be the third overall meeting between Djokovic and Raonic. They have yet to play on a hard court or a grass court, a fact that may help and hinder the Canadian. He knows the level of play he must bring to beat Djokovic on clay, but he will also realize that Djokovic has a good read on his serve and that his anticipatory skills will be put to better use on a slower surface.

It’s no secret that Raonic will be blasting first and second serves. Djokovic’s sensational returning skills mean that Raonic must hold absolutely nothing back when delivering his biggest weapon. It’ll also be important for Raonic to look to beat Djokovic with variety as well off the serve. Raonic can drill serves down the middle of the box all day long against most players and reap the benefits of weak returns and service winners. Varying placement and spin will prevent Djokovic from entering a returning groove, making it more difficult for him to connect on a higher quantity of returns.

Raonic will also need to move forward as much as possible in this match. Whether this means serving and volleying or taking anything short and coming forward, attacking the net is a must. As much as his ground play has improved, it’s nowhere near the level it needs to be to stay with Djokovic. Needless to say, Raonic’s approach shots will have to be of the highest grade unless he wants to be the victim of ceaseless Djokovic passing shots.

This moment is big—the biggest of Milos Raonic’s career. He carries the offensive artillery to pose a threat to Djokovic, as evidenced by their match in Rome. Don’t expect Raonic to win, but this may end up being a closer match than most expect.

Prediction: Djokovic in four sets

Ernests Gulbis vs. Tomas Berdych

Historically speaking, this has not been a favorable matchup for Ernests Gulbis. The Latvian has played Tomas Berdych six times, only coming out victorious twice. Adding insult to injury, Berdych has won three of their last four meetings, including their only meeting on clay.

Gulbis’s fourth-round five-set victory over Roger Federer should augment his already soaring confidence level. Gulbis is currently on an eight-match winning streak going back to his title run in Nice during the week prior to the French Open.

Berdych compiled a terrific returning performance against John Isner, taking out the big-serving American without having to play a single tiebreak.

For Gulbis, the stakes are extremely high in this match. If he can take out Berdych, he’ll not only cement his spot in his first Grand Slam semifinal, but he would rise into the top 10 for the first time in his career.

This is clearly a winnable match for both players, but Berdych will have the slight edge for several reasons. First, Berdych’s premier shot, his cross-court forehand, plays right into Gulbis’s weaker groundstroke, his forehand. Berdych’s technically sound backhand will also make it tougher for Gulbis to do damage with his favorite shot, his cross-court backhand.

With the serving being almost equal between these two, the return of serve will also be a huge factor. If one player is returning significantly better than the other, it would be difficult to believe they wouldn’t have the advantage. Again, one would suspect that Gulbis’s protracted forehand is going to give him a lot of trouble on the return of serve.

This one is as tough to pick as any match this year, but Berdych should be able to take care of business in four or five tight sets.

Prediction: Berdych in five sets