The US Open's Round of 16 in New York delivers a varied slate on Monday, September 7, featuring a rematch with a clear recent precedent, a completely fresh encounter, and a rivalry that has gone one win apiece. Here is a closer look at each matchup on the day's schedule.

Francisco Cerundolo vs. Alexander Blockx - Round of 16

Scheduled for approximately 4:00 PM EDT.

This Round of 16 clash carries meaningful recent history. The pair have met once before, with Blockx holding the only head-to-head win, a 7-6(8), 6-2 victory over Cerundolo in the Round of 4 at the Mutua Madrid Open in Madrid. That scoreline tells a clear story: Blockx took the opening set in a tight tiebreak before pulling away decisively in the second. Cerundolo enters ranked 27th in the world, while Blockx sits just 10 spots below at 37th, making this a closely matched contest on paper. With no odds available to signal a market favourite, and Blockx's only prior meeting going in his favour in convincing fashion once the tiebreak was settled, the Belgian must be considered a credible threat to advance.

Prediction: Blockx in three sets.

Karen Khachanov vs. Learner Tien - Round of 16

Scheduled for approximately 7:00 PM EDT.

This Round of 16 match is a true unknown heading in: Khachanov and Tien have never met on tour, leaving no head-to-head record to draw from. Khachanov enters ranked 15th, giving him a modest edge over Tien at 19th, though the gap is not dramatic. No odds are available to offer further market guidance. With no prior meetings and no additional data provided, this matchup must be assessed on rankings alone, where Khachanov holds the slight advantage.

Prediction: Khachanov in four sets.

Alexander Zverev vs. Luciano Darderi - Round of 16

Zverev and Darderi meet in the Round of 16 with their head-to-head series perfectly split at one win apiece, and both of those meetings came at the same tournament: the Internazionali BNL d'Italia in Rome. Zverev took the first encounter 7-6(3), 6-2 in the Round of 3, only for Darderi to reverse the result in the very next round, beating him 1-6, 7-6(10), 6-0 in the Round of 4. That second match in particular is striking: Darderi lost the first set heavily, forced an extended tiebreak in the second, and then dominated the decider. Zverev enters ranked 3rd in the world compared to Darderi's 18th, a substantial gap. No odds are available, but the ranking differential strongly favours Zverev despite Darderi holding the more recent head-to-head victory.

Prediction: Zverev in four sets.