This article originally appeared on The Grandstand.
(3) Roger Federer vs. Frances Tiafoe
Ricky: Tiafoe accounted himself extremely well in his only previous meeting with Federer, a 7-6(2), 6-3 loss earlier this season at the Miami Masters. But a showdown against the 19-time Grand Slam champion in Arthur Ashe Stadium is a whole different beast. It will be a good experience for the 19-year-old American, but also a tough one. If Federer’s back is even close to 100 percent, he is an obvious favorite to win this title. Federer in 3: 6-4, 6-2, 6-4.
Pete: Plenty of eyes will be on this match as the condition of Federer’s back will be under the scope, while concurrently a nation carefully watches the progress of a youngster who recorded the biggest victory of his career in defeating a fatigued Alexander Zverev in Cincinnati two weeks ago. We have seen young upstarts take the first set from the Swiss at majors in the past (John Isner at the 2007 U.S. Open and David Goffin at Roland Garros in 2012), but that is usually where the fun stops as Federer quickly corrects course. After a close opener, Federer will cruise. Federer in 3: 7-5, 6-2, 6-3.
Jeremy Chardy vs. (18) Gael Monfils
Ricky: This marks the third career ATP-level encounter between the two Frenchmen, with all three coming in the first round of a major. Monfils got the job done at the 2009 U.S. Open before Chardy prevailed in five sets at Wimbledon in 2016. Chapter 3 may not be high in quality, because Monfils is once again a question mark in terms of his health and Chardy has not played since leaving the All-England Club. Monfils loves New York, so he should coast if fit. Monfils in 3: 6-1, 6-3, 7-6(7).
Pete: New York, the world’s biggest stage…. Thus it comes as no surprise that the showman Monfils reached one of his two career major semifinal appearances in the Big Apple. Just last year, the acrobatic Frenchman won the first 15 sets he played before losing to Novak Djokovic in the semis. La Monf recently pulled out of Cincinnati, unfortunately raising the usual questions about his health and ability to compete. But Chardy, his countryman and opponent, has not played since Wimbledon and last recorded a win in June. Monfils has played a tiebreaker in six of his last seven matches but will not need to go that route this time. Monfils in 3: 6-3, 7-5, 6-4.
Ryan Harrison vs. (15) Tomas Berdych
Ricky: Berdych vs. Harrison is starting to get old–at least for Harrison. They have faced each other three times, all in the last 13 months, and all have gone the way of the Czech. He most recently beat the American 6-4, 6-3, 6-7(8), 6-3 earlier this summer at Wimbledon. Harrison is playing some of the best tennis of his career this season, but he simply does not have the same kind of firepower that Berdych possesses. The veteran may be past his prime, but he is quietly putting together a fine year. Berdych in 4: 6-3, 6-4, 3-6, 6-2.
Pete: Last year Berdych had to pull out of the U.S. Open, ending a streak of 52 consecutive appearances in majors. The Czech will certainly show some effects of rust coming into this one, having played just four matches since Wimbledon. Harrison had a nice run to the Atlanta final but has won only one match in three events since. Although the American has continued to improve in majors, the overall experience of Berdych will win out and the 2012 U.S. Open semifinalist will advance. Berdych in 4: 7-5, 3-6, 6-4, 6-2.
Marcos Baghdatis vs. (WC) Taylor Fritz
Ricky: Baghdatis and Fritz were one round away from going head-to-head last week in Winston-Salem, but Baghdatis fell to Roberto Bautista Agut and Fritz succumbed to the Spaniard one day later. Now the veteran and the youngster will square off on a much grander stage in New York. Fritz is slowly rounding into form after spending the early stages of 2017 working on fitness as opposed to getting matches under his belt. Baghdatis is also playing decent tennis and he reached the fourth round of the 2016 U.S. Open, but he is on the way down and Fritz is on the way up. It’s the American’s time. Fritz in 4: 7-5, 3-6, 6-3, 7-6(4).
Pete: Baghdatis reached the round of 16 last year in New York, matching his best result in a major since the 2009 Aussie Open. The Cypriot also notched a pair of wins at both Washington, D.C. and Winston-Salem. Meanwhile, Fritz is seeking his first win at a major in this, his seventh appearance. The young American recorded three solid wins in Winston-Salem last week and competed well in a loss against eventual champion Bautista Agut in the quarterfinals. The home crowd will help see the teenager through for his first major victory. Fritz in 4: 7-5, 6-4, 3-6, 7-6(5).
Fernando Verdasco vs. Vasek Pospisil
Ricky: This matchup would have been especially fun a couple of years ago. But Verdasco is past his prime and Pospisil is stuck in a prolonged rut–at least by the standards he set for himself with a run to the 2015 Wimbledon quarterfinals. The Spaniard has at least shown decent form of late, whereas Pospisil is a disastrous 1-6 in his last seven matches dating back to late June. Verdasco also dominated their only previous encounter 7-5, 6-0 early this season in Doha. Verdasco in 3: 6-4, 6-4, 6-4.
Pete: Despite back-to-back quarterfinals at the U.S. Open in 2009 and 2010, Verdasco has not managed to advance past the third round since. Meanwhile, Pospisil has picked up just two wins in five appearances at the annual last major of the year. Neither man has played particularly well in the last few months, which most likely makes this a tighter contest than it may appear on paper. The Spaniard will be able to execute better across the board on this day. Verdasco in 4: 6-3, 4-6, 6-2, 6-4.