Spots in the proverbial second week of Wimbledon will be at stake on Friday, when Tommy Paul goes up against Hubert Hurkacz in the third round. With no days off following his previous match, Jan-Lennard Struff faces Daniil Medvedev.
Hubert Hurkacz vs. (21) Tommy Paul
Paul and Hurkacz will be squaring off for the fifth time in their careers when they clash in round three at Wimbledon on Friday. The head-to-head series stands at 3-1 in favor of Paul, who has won three straight over Hurkacz after losing their first encounter on the indoor hard courts of Paris in 2021. Their most recent meetings came at the Rome Masters in both 2024 and 2025, with Paul prevailing 7-5, 3-6, 6-3 and then 7-6(4), 6-3.
A grass court certainly gives Hurkacz a better chance. The 96th-ranked Pole is a former Wimbledon semifinalist (2021) and reached the fourth round in 2023. Alarmingly, however, he had not advanced past round two of any Grand Slam since the 2024 French Open before beating Casper Ruud and Sebastian Ofner earlier this week. Those are decent straight-set results, but don’t forget that facing Ruud on grass is nothing more than a virtual bye. Paul is in far better form, as he finished runner-up at Queen’s Club and then completely destroyed Alexandre Muller and Soonwoo Kwon to begin his Wimbledon campaign. The 25th-ranked American is a superior all-court player these days, so Hurkacz will be in trouble unless he delivers one of the best serving performances of his career.
Pick: Paul in 4
Jan-Lennard Struff vs. (8) Daniil Medvedev
Struff was seemingly on his way out of the tournament on Thursday afternoon. Brandon Nakashima had not been broken in the entire match when he stepped to the line to serve for it at 5-4 in the fifth set. From completely out of nowhere, though, Struff broke to stay alive and ended up triumphing 4-6, 7-6(6), 7-6(5), 6-7(6), 7-6(10-7) after four hours and 21 minutes. Only the fifth set took place on Thursday after the match was postponed by darkness on Wednesday evening, so fatigue should not be a serious factor for Struff.
Next up for the 36-year-old German is a 12th showdown against Medvedev, who is dominating the head-to-head series 9-2 (8-1 on the main tour). They have met twice on grass, with Struff prevailing 7-6(6), 6-3 at the 2021 Halle tournament before Medvedev got the job done in a fourth-set tiebreaker at Wimbledon in 2024. The ninth-ranked Russian has been all over the place in 2026, but he at least managed to win multiple matches in both ‘s-Hertogenbosch and Halle and has already done the same at the All-England Club with routine victories over Marin Cilic and Daniel Merida. Medvedev’s defense has almost always gotten the best of Struff’s offense, so there is no real reason to think that anything will be different this time around.
Pick: Medvedev in 4
