As the remaining players in the draw fight for a spot in the final, we preview and predict three must-see matches in Key Biscayne.

They’ve been on tour together for nine years, but somehow these two crowd favorites have faced each other just once: Two years ago on grass in Halle, Nishikori beat Monfils in three sets. This will be a higher-profile meeting, and will come on a slow hard court that should be favorable to both players. It's a big opportunity for both of these guys: Between the two of them, they’ve reached just three Masters finals, and have never won any; Nishikori, in particular, is beyond due at this level. Now they have a chance not only to reach a semifinal, but to avoid playing one of the Big Four if they do—the winner of this match will face either Milos Raonic or Nick Kyrgios. Monfils has been more focused this year, a trend that continued with his fourth-round win over Grigor Dimitrov here. But Nishikori, on most days, is the better player.

Winner: Nishikori

The serves will be fast and the rallies brief in Thursday’s first night match: Blink too often and you might not see any points at all. These two bomb throwers have faced off three times. Raonic won the first two, at the French Open and Wimbledon in 2014; Kyrgios turned the tables last year at the All England Club. As is the case for Nishikori and Monfils, this match represents an unprecedented opportunity for both: The 25-year-old Raonic has been to three Masters finals and won none; the 20-year-old Kyrgios is still looking to go deep at this level for the first time. A triumph here would seem to be the natural springboard to future Grand Slam success for both. Kyrgios has more all-around ball-striking talent, but Raonic has narrowed that gap so far this season. The Canadian is the safer bet, but so far in Miami the Aussie has looked ready to take advantage of his wide-open draw.

Winner: Kyrgios

Azarenka is 6-1 against Kerber, but that doesn’t do justice to what many people are expecting from this match. These two have played two classics. At the WTA Championships in Istanbul in 2012 and at the U.S. Open last year, Azarenka finished titanic struggles by winning 6-4 in the third set. But Kerber may have won their most important meeting: In the quarterfinals at this year’s Australian Open, she beat Azarenka for the first time and went on to win her first Grand Slam title. There’s a reason their matches have been so good: Vika is one of the game’s great attackers; Angie is one of the world’s great defenders. Together their rallies can work magic.

Winner: Azarenka