The 2026 Wimbledon Championships has delivered a fantastic draw, with some of the first-round matches not to be missed. Defending champion Jannik Sinner isn’t featured in this article as he has a relatively straightforward match against Miomir Kecmanovic. But the drama lies elsewhere. An injury returnee who is also the home favourite will take on one of the best players on grass. A matchup between a legendary veteran on his farewell tour against a former finalist and many more intriguing matches.
Here are the five standout men’s first-round matches that promise the most excitement on the grass of SW19.
Five Best Men’s First Round Matches: 2026 Wimbledon
Taylor Fritz vs Jack Draper
This is the headline blockbuster of the first round. American sixth seed Taylor Fritz, who is one of the best players on this surface and in superb form, will take on the biggest home hope, Jack Draper. This is a brutal match for both, considering they were top-five seeds at the 2025 Wimbledon. This match could easily be a quarterfinal if not for Draper’s fall in ranking.
Draper reached a career-high ranking of No. 4 in 2025, has battled injuries, and just returned on tour in Eastbourne after over two months of absence. Only worse players he could have drawn would be Jannik Sinner and Novak Djokovic. Wimbledon has never been a successful tournament for Draper, but he had fewer expectations this time due to his injuries, which would have helped him play freely. However, being an underdog in this match could still free him up and potentially bring out his best tennis.
As for Fritz, he decided to withdraw from the tournament in Eastbourne to rest after two successive finals in Stuttgart and Halle. He is on Alexander Zverev’s half of the draw and is probably the favourite to reach the final with his success and calibre on this surface. So an early exit would be catastrophic for the American. This match is almost certain to be played on the Centre Court, and fans can expect pure grass-court theatre.
Daniil Medvedev vs Marin Cilic
Two US Open champions, Daniil Medvedev and Marin Cilic, will meet for the sixth time in their career and for the third time on grass. Cilic is in the twilight years of his career, but he is still capable of taking the racquet out of his opponents’ hands, especially on this surface. He is a former finalist here and made a great run to the fourth round last year.
Medvedev, the eighth seed and two-time Wimbledon semi-finalist, has had two disappointing losses on grass in the build-up to 2026 Wimbledon. He knows he has to play his best tennis to win this match, as Cilic’s experience on grass and big-match mentality make him a very dangerous opponent. Cilic’s serve and first strike tennis is good enough to keep this close, and Medvedev hasn’t been particularly clutch in the last two years when his opponent has pushed him, so it’ll be intriguing to see how he reacts under pressure. The last time these two played here, the match went to a deciding set, and there’s a high chance of another competitive match.
Stan Wawrinka vs Matteo Berrettini
This is the most emotionally charged match of the first round. Three-time major champion Wawrinka is playing in his final season on tour. A wild card at 2026 Wimbledon gives the Swiss legend one last chance to compete at the All England Club, where he has reached the quarter-finals twice. Standing in his way is Matteo Berrettini, the 2021 Wimbledon finalist and a proven grass-court specialist with multiple titles at Queen’s Club. Berrettini has been one of the most injury-prone players in the last five years, but is still a threat to basically anyone on the tour when healthy.
For Wawrinka, this is about enjoying one final SW19 appearance and soaking up all the applause and love. For Berrettini, it will be a chance to show not only the world but also to himself that all the work and grit he has put in after every setback is worth it. This is a must-watch.
João Fonseca vs Roberto Bautista Agut
Joao Fonseca, the 19-year-old Brazilian seeded No. 24, is making his second Wimbledon main-draw appearance. He reached the third round in his 2025 debut and has shown massive potential in his short career. Fonseca made headlines with a big run at Roland Garros 2026 (including notable wins over Novak Djokovic and Casper Ruud).
He has played one grass-court match this season, and his performance was dismal to say the least. However, with his improved net game, massive serve, and forehand, he should pose a threat if he can adapt quickly. And he will need to adapt soon since the 38-year-old Roberto Bautista Agut will be a formidable first-round opponent.
The Spaniard, who is playing in his final season, is a former Wimbledon semifinalist with a strong history on grass despite his lower ranking and limited form in 2026. He has been one of the walls of Spanish tennis over the last decade, and this being his final Wimbledon adds extra sentimental value to this contest.
Casper Ruud vs Hubert Hurkacz
It’s no secret that Casper Ruud doesn’t rate the grass season much, and any match wins at Wimbledon are a bonus for him. He has never advanced past the second round here, but he has won first-round matches in his last three appearances and will be looking to match, if not exceed, that record. A match win or two could help Ruud on his quest to enter the top-10 once again. However, his first-round streak is in big danger as he will face Hubert Hurkacz, who is actually pretty good on grass.
Wimbledon has been Hurkacz’s most successful Grand Slam and his only Slam where he has reached a semifinal. However, the Polish player is going through the worst phase of his career with a season win percentage of 43, his worst since 2018. Even on grass, which is his favourite surface, he has underperformed. This makes 2026 Wimbledon bigger and more important than ever for Hurkacz. An early exit could dent his confidence even more, but a good start could pave the way for a resurgence.
Notable Mentions
- Alexander Zverev vs Alexander Blockx
- Andrey Rublev vs Roman Safiullin
- Alexander Bublik vs Thanasi Kokkinakis
- Arthur Fils vs Raphael Collignon
- Jiri Lehecka vs Alexei Popyrin
Main Photo Credit: Mike Frey – Imagn Images
