Nick Nemeroff continues his Rome previews by looking at the challenges ahead of the top two men, both of whom survived three-set battles on Friday.

Novak Djokovic v. Milos Raonic

The ballistic, missile-like serve of Milos Raonic will meet the finest returner in the game, Novak Djokovic. Raonic and Djokovic previously met in Davis Cup last year, a match played on clay and won by Djokovic in straight sets.

Raonic’s 2014 season has been extremely successful. The Canadian achieved his career-high ranking of No. 9 on April 21 and has made the quarterfinals at four of the five Masters 1000 events he has played this season. Djokovic’s 2014 Masters 1000 campaign has been even more prosperous. If not for a bad wrist, he may have claimed three or four Masters 1000 crowns as opposed to the two he won in Indian Wells and Miami.

The combination of surface and opponent is less than ideal for Raonic. Djokovic is one of the few returners in the game who is consistently able to put Raonic in uncomfortable positions when serving.  In addition, points of any significant length favor Djokovic, so Raonic’s offensive-oriented game will have a tough time breaking through against him on clay. All of Raonic’s weapons will have less penetrating power, and against an opponent that defends as well as Djokovic, this is a recipe for disaster.

If I was Raonic, I would watch and learn from the two victories that John Isner had over Novak Djokovic in Cincinnati last year and in Indian Wells in 2012. Considering Raonic and Isner play virtually identical games, the Canadian would be wise to integrate aspects of Isner’s game plan into his own.

Raonic has had a great tournament and will use this week as a building block to further success, but he’s more likely to be eating pasta and doing sightseeing on Sunday than playing in the final.

Prediction: Djokovic in two sets

Grigor Dimitrov v. Rafael Nadal

In the second men’s semifinal, the King of Clay will be seeking his second straight Masters 1000 final as he takes on a rising men’s talent. Dimitrov and Nadal have played on four separate occasions with each match going to Nadal—but not without some resistance from the Bulgarian. Dimitrov has won one set in all four matches he’s played against Nadal, including a quarterfinal in Monte Carlo last year. Nadal and Dimitrov last met in the quarterfinals of the Australian Open, in what was arguably one of the best matches of the entire 2014 season. Nadal won this match in four sets after fighting back from a set down.

Dimitrov enters this match having had to play only one set in his quarterfinal match against Tommy Haas before the German was forced to retire due to a shoulder injury. Dimitrov was on court for a total of 36 minutes. Compare this to Nadal, who was on court for two hours and 40 minutes in his three-set victory over Andy Murray.

In their previous matches, Dimitrov has done well to handle Nadal’s cross-court topspin forehand with his one-handed backhand. He has countered the depth and spin of Nadal’s forehand with his wonderful capacity to step in and drive through his backhand. In addition, Dimitrov’s proficient lateral movement and effective defensive slice backhand allows him to handle the width and angles that accompany the Nadal forehand.

We’ve seen some substantial stretches of passivity from Nadal in the last few matches, but against someone who is able to control the action as well as Dimitrov, Nadal will be less inclined to yield the initiative. Expect him to come out firing on all cylinders in this one.

One play that would serve Dimitrov well that Andy Murray probably could have used with more frequency against Nadal is the serve and volley. With the Spaniard standing great lengths behind the baseline to return, Dimitrov’s booming serve will provide him with an abundance of opportunities to move in and end points with conviction and efficiency.

All three of Nadal’s matches this week have lasted over two hours and 40 minutes. Having seen what inroads Nadal’s adversaries have been able to make against him this week and previous ones, Dimitrov will come into this match as confident as ever. Kei Nishikori is a young gun who made his first Masters Series 1000 final last week. Don’t be surprised if Grigor Dimitrov achieves the same feat tomorrow.

Prediction: Dimitrov in three sets