How to watch: ESPN, 9 p.m. Eastern; streaming on ESPN+ and ESPN3, 9 p.m.
Roger Federer vs. Tennys Sandgren
On his way to Monday night’s quarterfinal match at this Australian Open, third-seeded Roger Federer, a 20-time Grand Slam tournament winner, did not play a seeded player. Although he struggled in his third-round match against John Millman, Federer looked fresh and decisive in his other three victories. Even when a portion of Federer’s game is not up to par, it can still rise above even other world-class players. Forehand errors defined the third-round match, but Federer won it off a forehand winner on a point in which Millman had pressed him into a poor position.
Federer’s opponent on Monday, Tennys Sandgren, is also unseeded, but he has beaten two seeded players. Sandgren, an American ranked 100th in the world, relied on his powerful serve to get past the Italians Matteo Berrettini and Fabio Fognini, the eighth and 12th seeds at the Australian Open.
Sandgren’s only other quarterfinal appearance in a Grand Slam event was at the Australian Open in 2018. To reach the semifinal, he will have to defeat a beloved six-time Australian Open champion in Federer. It seems unlikely that the Melbourne crowd will be rooting for the underdog.
Ashleigh Barty vs. Petra Kvitova
Ashleigh Barty of Australia, the world No. 1, has been hot and cold the first week at the Australian Open. She dropped two sets on the way to the quarterfinals, but it seems that winning the French Open last year has given her some tenacity when she’s not playing her best. It’s this experience that she hopes will help her advance past the quarterfinals, even though she faces Petra Kvitova, who knocked her out at this stage 12 months ago.
Kvitova, a two-time Wimbledon winner, reached the final of the Australian Open last year before losing to Naomi Osaka. After skating through her first three rounds this year, she needed three sets to beat Maria Sakkari, the 22nd seed. Since last year’s Australian Open, Kvitova has lost three times to Barty, and it may seem a foregone conclusion that the Australian’s home-court advantage will help her secure a win. But Kvitova is still the veteran player, and has a knack for pushing players into the deep corners of the court and coming in to cut off any subpar responses at net. No matter the score, it’s sure to be the most entertaining match of the night.
Novak Djokovic vs. Milos Raonic
Novak Djokovic, the second seed, has dropped only one set on his way to the quarterfinals. Djokovic, 32, is the youngest of the so-called Big Three, and is considered by many to be the favorite in this year’s Australian Open. In his quest to push his game to the limits, he often hits shots on the slide, well outside the edges of the court, breaking down his opponents by making them hit three exceptional shots before they get into place to hit a winner against him.
Milos Raonic, who fought past a resurgent Marin Cilic in the last round, has looked exceptional through the first week of the Open. Raonic’s powerful groundstrokes allow him to dictate longer rallies, and his height gives his serving a clear advantage. Raonic hit 35 aces against Cilic and 19 against Stefanos Tsitsipas in his third-round upset of the sixth seed.
Although Djokovic, a seven-time Australian Open champion, is considered the greatest returner of serve in the modern game, Raonic has an opportunity to take away that weapon and power past him.
Sofia Kenin vs. Ons Jabeur
Ons Jabeur, ranked 78th in the world, is the first Arab woman to reach the quarterfinals of a Grand Slam event. Jabeur, a Tunisian, reached the third round of a major at the 2019 United States Open and the 2017 French Open. After beating Johanna Konta, the 12th seed, in the first round, Jabeur took out Caroline Wozniacki, the former world No. 1 who is retiring after this year’s Australian Open, and 27th-seeded Wang Qiang. She will try to force another upset, this time over 21-year-old Sofia Kenin.
Kenin, the 14th seed, has reached her first Grand Slam tournament quarterfinal. Although she has not faced a seeded player in the tournament, she defeated Coco Gauff, the exceptional 15-year-old, in the round of 16 on Sunday. With a combination of cautious shot selection in longer rallies and powerful counterpunching on the run, Kenin has a way of forcing her opponents into uncomfortable shot selection. This may be an especially hard problem for Jabeur to overcome. In Jabeur’s last three rounds, she has hit more unforced errors than winners, and to make matters worse, swinging big is rarely the solution against quick counterpunchers.