Wimbledon: Six Popcorn First-Rounders on the Men’s Side

The Wimbledon men’s singles draw delivered a bevy of first-round popcorn matches, including a clash of former Grand Slam champions and a former Wimbledon finalist against a living legend.

Matteo Berrettini vs Stan Wawrinka

The only former Wimbledon finalist in the bottom half of the draw meets the Stanimal in a first-rounder to die for. How is it that these two have never met on tour?

A pair of fan favorites, with one bidding farewell to the All England Club, should have plenty of fans feeling nostalgic in round one.

Marin Cilic vs Daniil Medvedev

In a rematch of their ’s-Hertogenbosch quarterfinal a few weeks ago (won by Medvedev in three sets), former runner-up Cilic will look to earn his second career win over the Russian in six meetings.

In their only previous Wimbledon meeting, Medvedev prevailed in five tight sets in the third round in 2021. That victory carried him into the round of 16 at SW19 for the first time. Since then, he has reached multiple semifinals, but arrives this year on the heels of a first-round loss to Benjamin Bonzi.

2017 runner-up Cilic carries a career record of 34-14 on Wimbledon’s grass. Will the 37-year-old turn back the clock?

Roberto Bautista Agut vs Joao Fonseca

Spaniard Roberto Bautista Agut, a Wimbledon semifinalist in 2019, is also saying goodbye in London this year. The 38-year-old will face Brazilian sensation Joao Fonseca, who reached the third round on his Wimbledon debut last year but lost his only grass-court match this season, 6-2, 6-2 to Yannick Hanfmann in Halle.

Former World No.9 Bautista Agut, currently ranked No.163, has yet to win a tour-level match on grass this season.

Taylor Fritz vs Jack Draper

Taylor Fritz cannot be thrilled with his draw. Typically, drawing the World No.160 in the first round is a gift, but when that player is a former World No.4 on the comeback trail and rapidly finding his form, it’s easy to see why this may be the toughest opener sixth-seeded Fritz could have drawn.

Not that the American can’t handle the challenge. He displayed resurgent form in reaching the Halle final last week, but Draper owns a 3-2 edge in the head-to-head and won their only previous meeting on grass.

Arthur Fils vs Rafael Collignon

Arthur Fils could find himself in a physical battle as he returns to the Grand Slam stage after missing Roland Garros due to injury. Fils reached the round of 16 at Wimbledon in 2024, and if healthy, he can be a force on grass.

But he hasn’t played a match since Rome, and Collignon is the type of player who makes opponents earn every point. The rising Belgian, now ranked a career-high No.43, pushed Alexander Zverev to two tight tiebreaks in Halle just last week before bowing out in the quarterfinals.

Alexander Zverev vs Alexander Blockx

Speaking of Alexander Zverev, how will the newly crowned major champion handle his new status? We’ll find out quickly as a talented young Belgian with a powerful game looks to give the 2026 French Open champ an uncomfortable opening test.

Blockx, who was forced to withdraw from Roland Garros with an ankle injury, has been one of the revelations of the 2026 season. If healthy, he has the tools to make life difficult for Zverev, who has reached the second week at Wimbledon three times but never gone beyond the fourth round.