ATP columnist Nick Nemeroff focuses on the three most important men’s matches to watch as the first week of the Australian Open concludes.

Grigor Dimitrov vs. Milos Raonic

With Juan Martin Del Potro’s stunning second-round loss at the hands of Roberto Bautista Agut, rising stars Grigor Dimitrov and Milos Raonic have been presented with a golden opportunity to reach the quarterfinals of a grand slam. Neither player has yet achieved this feat in their young, rapidly progressing careers.

The importance of this match cannot be overstated. Not only will the victor move forward to the fourth round but will also be favored to reach the last eight regardless of whether they face Benoit Paire or Bautista Agut.

Both players have taken advantage of favorable draws and experienced minimal adversity during their first two matches. With temperatures expected to cool down considerably in Melbourne, Dimitrov and Raonic will be happy knowing they won’t have to deal with near unplayable conditions for yet another match.

They have met on only two prior occasions in ATP matches. Raonic won their first meeting back in 2011 in Stockholm, and Dimitrov won their most recent meeting last year in Brisbane. Both matches ended in two sets.

The game plan for Dimitrov is simple: get as many serves back into play as possible. Once engaged in a rally, Raonic is far less effective. Dimitrov will be looking to block and chip back a high quantity of deep returns to prevent Raonic from commanding the center of the court with his forehand/serve combinations.

As challenging as it will be for Dimitrov to break Raonic, he’ll have the comfort of knowing that the Canadian’s return skills aren’t anything special and that his own serve is no pushover either.

Prediction: Dimitrov in four sets

Jo-Wilfried Tsonga vs. Gilles Simon

In the ongoing drama that is Gilles Simon’s 2014 Australian Open, the Frenchman will look to score his most improbable victory yet as he takes on his flashily entertaining countryman, Jo-Wilfried Tsonga.

The man who was walking on crutches several days before the start of the tournament has miraculously pushed through two five-set matches against German Daniel Brands and Croat Marin Cilic. Against Brands, Simon was on the brink of defeat and needed to overcome seven match points.

Tsonga’s first two matches included straight-sets victories over Filippo Volandri of Italy and Thomaz Bellucci of Brazil.  Tsonga leads the head-to-head 5-4 and leads 5-1 on hard courts against Simon. He won their last match on the hard courts of Metz last fall in straight sets.

It’s pretty safe to say that Tsonga will come into this matchup with an abundance of energy, while Simon may come on to court in a stretcher. As flamboyant and electric as Tsonga is, that’s how unmoving and steady Simon is:  a true study of contrasts.

Their differing on-court demeanors and attitudes may stem from their polar opposite playing styles. Tsonga is a power merchant through and through. His desire to strike magnificent winners causes him to attempt shots that range from the sublime to the ridiculous. Simon, by contrast, is the epitome of a human backboard. While many players are often called human backboards for their consistency, it is typically a moderate-to-vast exaggeration. For Simon, it’s pretty close to the truth. This guy simply doesn’t miss.

When you mix Simon and Tsonga, you get a few hours of one player trying to hit winners and the other trying to stop him. Whether Simon has the physical resources left to play this role is uncertain, but the lower-ranked Frenchman will also need to worry about his second serve. If Simon’s second serve, the biggest vulnerability in his game, sits up short in the box, Tsonga is going to break early and often. 

This match seems to be perfectly set up for a fairly comprehensive Tsonga win, but with Simon, nothing is ever set in stone.

Prediction: Tsonga in three sets

Rafael Nadal vs. Gael Monfils

Nadal, while the favorite in this rematch of the Doha final, should be wary of what the enigmatic Frenchman can do on a fast hard court. Monfils, who has only made the fourth round of the Australian Open on one occasion, will need to use his immense talents to their full extent if he wants to take down the top seed and earn a spot in the fourth round.

Nadal won his first two matches against young Aussies Bernard Tomic and Thanasi Kokkinakis, while Monfils won his first two matches against young Americans Ryan Harrison and Jack Sock. Both Nadal and Monfils have yet to drop a set.

Nadal leads the head-to-head 9-2 and defeated Monfils in their only prior grand slam encounter, which was in the fourth round of the 2009 US Open.

Monfils has led a career criticized for not meeting expectations. At age 27, the amount of opportunities he will have to test the world’s best may be dwindling. Monfils will need to use his height and technically sound backhand to neutralize Nadal’s cross-court forehand. In addition, he’ll have to use his far-reaching wingspan to reduce the effectiveness of Nadal’s spin serve out wide. It will also be important for Monfils to rack up the ace count and go big on his second serve. Any opportunity to take Nadal out of a rally must be seized. 

There aren’t many players who can consistently duel with Nadal from the baseline, but Monfils is one of them. If he can find the Nadal backhand, and take his chances but not get too wild, he’ll be giving himself a fighting chance in this match.

Monfils would also be wise to playing attacking tennis and move forward on a regular basis. By doing this, he’ll be equipping himself with yet another option by which to finish points.

As far as Nadal is concerned, he’ll be content with executing his typical patterns but will need to ensure he hits with consistent depth, for Monfils will be primed to pounce on any short ball. It’s hard to predict the outcome because we never know how Monfils is going to play, but if Nadal comes out and plays his standard game, he should prove to be too much.

Prediction: Nadal in four sets