The first quarterfinal spots will be handed out at Wimbledon on Sunday, when a blockbuster matchup features Daniil Medvedev and Grigor Dimirov. A red-hot Tommy Paul is going up against Roberto Bautista Agut.
(10) Grigor Dimitrov vs. (5) Daniil Medvedev
Medvedev and Dimitrov will be facing each other for the 11th time in their careers when they meet again in round four at Wimbledon on Sunday. The head-to-head series stands at 7-3 in favor of Medvedev, who has won four of their last five encounters dating back to the fall of 2022. They have squared off once this season, when the Russian rolled 6-4, 6-4 on his way to a runner-up performance at the Indian Wells Masters. Their only previous grass-court contest marked the fist time they ever locked horns; Dimitrov scored a 6-3, 3-6, 6-3 victory at the 2017 Queen’s Club tournament.
Both men boast stellar lifetime records on grass and have been to the Wimbledon semifinals once (Medvedev in 2023, Dimitrov in 2014). If the surface favors either player, it’s Dimitrov; Medvedev likes the ball higher in his strike zone and his forehand takes a pretty long time to develop, while Dimitrov’s backhand slice is especially effective on the slow stuff. Each man battled through one especially tough match in the Wimbledon second round; Medvedev came back from a set and a break down to beat Alexandre Muller, while Dimitrov erased a daunting two-set deficit against Jerry Shang. Playing on a favorable surface and enjoying one of the best seasons of his illustrious career, Dimitrov may have a slight edge in what should be an extremely competitive and entertaining affair.
Pick: Dimitrov in 5
(12) Tommy Paul vs. Roberto Bautista Agut
Paul has been one of the best players on grass this summer; in truth he has been outstanding all year long regardless of the surface. The 27-year-old American is one spot off his career high at No. 13 in the world thanks in part to semifinal showings in Indian Wells and Rome, a runner-up finish in Delray Beach, and titles in Dallas and Queen’s Club. Paul has improved to 9-1 on grass in 2024 with wins this fortnight over Pedro Martinez, Otto Virtanen (five sets), and Alexander Bublik.
Up next for the 12th seed is a sixth showdown against Bautista Agut, who leads the head-to-head series 3-2 but has lost two in a row. They most recently squared off at the 2023 Australian Open, where Paul prevailed 6-2, 4-6, 6-2, 7-5. It’s no surprise that the tide of this matchup has turned, as Paul’s rise has coincided with Bautista Agut’s decline. The 36-year-old Spaniard is struggling down at No. 112 in the world. He loves grass and has done well to capitalize on a favorable draw with defeats of Maximilian Marterer, Lorenzo Sonego, and Fabio Fognini, but his upcoming opponent represents a steep climb in competition level. Bautista Agut also doesn’t win a ton of free points on serve, which generally spells disaster against Paul.
Pick: Paul in 3