(2) Andy Murray vs. (22) Grigor Dimitrov
Dimitrov has been enjoying a resurgence this summer, posting a 10-4 record on hard courts. Murray leads their head-to-head by 6-3, but Dimitrov has beaten him twice on hard courts and prevailed in their most recent meeting, this March at the Miami Open. Murray looked spotty in his four-set win over Paolo Lorenzi on Saturday, but he always raises his level in the second week of Grand Slams. Expect the No. 2 seed to be pushed early but to find another gear to prevail in four sets.
(3) Stan Wawrinka vs. Illya Marchenko
Wawrinka is lucky to be here after fighting off a match point in his third-round win over Dan Evans, but Marchenko is in the same boat after defeating an ailing Nick Kyrgios via retirement. Minus the win over Kyrgios, Marchenko hasn’t beaten a Top 50 player since January. Wawrinka comfortably won their only previous meeting this March and the same will take place on Monday. Wawrinka in three sets.
(6) Kei Nishikori vs. (21) Ivo Karlovic
With his huge serve, Karlovic is a player that nobody wants to face. But if anybody has to, a player with a solid return like Nishikori is a perfect choice. Although Karlovic leads their head-to-head by 2-1, one of those wins was by retirement and they haven’t played in more than two years. It’s also safe to say that Nishikori is a much different player from the last time they squared off. Karlovic did well to achieve his best US Open result ever this tournament, but Nishikori will advance in four sets.
(8) Dominic Thiem vs. (WC) Juan Martin del Potro
Del Potro has modestly passed Thiem off as the favorite in their upcoming match, but the Argentine won their only previous meeting this May on the clay courts of Madrid. He’s also in red-hot form, while Thiem has had a relatively modest summer for his recent standard. There will be plenty of entertaining rallies in this match, but del Potro will prevail in four sets.
(1) Serena Williams vs. Yaroslava Shvedova
A win on Monday will give Serena 308 Grand Slam singles wins, more than any other tennis player in history. She leads her head-to-head against Shvedova by 4-0. Although she’s not immune to shocking upsets in New York (see: Roberta Vinci), it won’t happen here. Serena in two sets.
(4) Agnieszka Radwanska vs. Ana Konjuh
Radwanska and Konjuh were deadlocked at 7-7 in the third set of their second-round match this year at Wimbledon, when the Croat turned her ankle after stepping on a ball. She’s looking for a chance to gain revenge now and has been in top form throughout the tournament. Radwanska has inexplicably faded at the fourth-round stage of the US Open throughout her career, posting an 0-4 record. But she’s feeling confident after prevailing two weeks ago in New Haven and appears ready to finally right the ship. Radwanska in three tough sets.
(5) Simona Halep vs. (11) Carla Suarez Navarro
Fans watching this match better pack a lunch because it’s guaranteed to go the distance. The pair are even in their head-to-head at 5-5, and seven of those matches have gone three sets. Halep leads their head-to-head on hard courts by 4-1, but Suarez Navarro’s lone win came in the second round of the 2011 US Open. The Spaniard will have her chances to take the match, but Halep will come through in three long sets.
(6) Venus Williams vs. (10) Karolina Pliskova
Venus has seemingly turned back the clock a decade this tournament, producing two routine wins in Arthur Ashe Stadium in her past two matches. She’s also in familiar territory at the second week of a Grand Slam, while the big-serving Pliskova is in the fourth round at a major for the first time. She’s done well to overcome that hurdle, but Venus will prevail in two tight sets.
Matt Cronin's Pick of the Day: Venus Williams vs. Karolina Pliskova
Venus Williams will face off against No. 10 Karolina Pliskova, and it should be a heck of a match. The two have played only once, back in the fall, when the American overcame the Czech in Zhuhai, China, 7-5, 7-6. Pliskova is very powerful, and she catches fire, but she is somewhat slow and can check out on occasion. Still, she has played better during the past month; in Cincinnati, she beat Garbiñe Muguruza and Angie Kerber to win it all.
Pliskova lost in the third round at the Australian Open, she reached the semis in Indian Wells and the quarters of Stuttgart. She didn't do much on clay, but on grass, she won Nottingham and reached the final at Eastbourne before losing early at Wimbledon. So far this Open, she has been very consistent and crushing the ball. She has a huge serve and she is willing to go for the lines.
Venus, however, knows the US Open inside and out, having won two titles but also lost some amazing matches. She was, and is, locked in.
So who wins? Venus is the favorite, slightly. She has improved over the past two years, and is still learning at age 36. She may not be fast as she used to be, but she is intelligent on court and can crack the ball when she wants to. Yes, Pliskova won’t give in. But Venus is on rhythm and will be patient. It will take two hours-plus, but the two-time champion will win, 7-5 in the third set.