Wimbledon 2026: The Top 12 First-Round Matches You Cannot Miss
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The official draw for The Championships 2026 is out! Tennis fans around the world are getting ready for two weeks of incredible sports action at Wimbledon. While the finals at the end of the tournament are always exciting, the very first round brings its own special drama. This year, we have legendary champions making surprise comebacks, rising teenage stars trying to make history, and major injury mysteries.
Here is a detailed guide to twelve must-watch first-round matches—six from the men’s (gentlemen’s) singles and six from the women’s (ladies’) singles. We will look at why these matches are so special and what to watch out for.
The Gentlemen’s Singles: Big Serves, Legends, and Rematches
1. Taylor Fritz vs. Jack Draper
This match brings together two players who hit the ball very hard and serve with incredible power. Playing on grass fits their styles perfectly, and they already have a history together at Wimbledon and other grass tournaments.
Back in 2022 at Queen’s Club, a young British player named Jack Draper shocked Taylor Fritz. It was the biggest win of Draper’s early career. Since then, they have played each other five times, and Draper leads their rivalry with 3 wins to 2. However, both players have been struggling with bad injuries recently.
Draper missed several weeks of tennis due to a knee injury and only returned to playing this week in Eastbourne. Even though he has been away, he looks in great shape. This year, Draper has a secret weapon: the legendary British champion Andy Murray is now working as his coach! Fritz is also recovering from a tough clay-court season and had to pull out of Eastbourne to protect his body. He reached two finals on grass earlier this month in Stuttgart and Halle but lost both. If both men are healthy, this will be an absolute battle of big serves.
2. Stan Wawrinka vs. Matteo Berrettini
This match is all about a legendary player saying goodbye. When the 41-year-old Stan Wawrinka played his very first Wimbledon in 2005, today’s top tennis stars were just toddlers! Now, the 2026 season will be Wawrinka’s final year on the professional tour. This is his 19th and last time playing at SW19.
Wawrinka is a three-time Grand Slam champion and a huge fan favorite because of his beautiful, powerful playing style. He has reached the Wimbledon quarter-finals twice. His opponent, Matteo Berrettini, knows exactly what it takes to win on these grass courts because he reached the Wimbledon final in 2021. Unfortunately, Berrettini has suffered from many injuries since then. Just recently, a hip injury forced him to quit during his French Open quarter-final. Fans will flock to see if Wawrinka can get one last big win, or if Berrettini’s powerful grass-court game will be too much to handle.
3. Marin Cilic vs. Daniil Medvedev
This is a clash between two giants of the game—literally, as both players stand at 6 feet 6 inches tall! Both have experienced great joy and deep disappointment on the lawns of Wimbledon.
Marin Cilic is a veteran who reached the Wimbledon final back in 2017, where he lost to Roger Federer. Since that great run, Cilic has struggled, winning only seven matches at Wimbledon over the last nine years. On the other side, Daniil Medvedev reached the semi-finals in 2023 and 2024 but suffered a shocking first-round loss last year. These two already played against each other on grass just a couple of weeks ago in ‘s-Hertogenbosch. Medvedev won that match in three sets and went on to reach the semi-finals. Cilic will be hunting for revenge, while Medvedev wants to make sure he does not lose early two years in a row.
4. Casper Ruud vs. Hubert Hurkacz
Hubert Hurkacz is famous for his incredible grass-court skills and his polite personality. Tennis fans remember 2021 when Hurkacz defeated the legendary Roger Federer in the quarter-finals, which sadly turned out to be Federer’s last-ever match at Wimbledon.
Even though Hurkacz is currently ranked lower at number 95 in the world, many experts think he is the favorite to win this match. His big serve and excellent net play are perfect for grass courts. His opponent, Casper Ruud, is the number 11 seed, but grass has always been his weakest surface. In five visits to Wimbledon, Ruud has never managed to get past the second round. This match will test whether Ruud has finally figured out how to move and play on grass, or if Hurkacz will pull off another famous Wimbledon victory.
5. Thanasi Kokkinakis vs. Alexander Bublik
It has been eight long years since Thanasi Kokkinakis and Alexander Bublik last played each other. The Australian, Kokkinakis, won that match, but both players have changed a lot since then.
Kokkinakis had a major pectoral surgery last year and has been slowly trying to rebuild his career. He showed great fighting spirit at the French Open this year with a massive comeback win, but his body broke down in the next round. When he is healthy, his powerful game can scare anyone. He will need all his power against Alexander Bublik, the number 10 seed. Bublik is famous for being “mercurial”—which means he is highly unpredictable, incredibly talented, and can hit shots that no other player would even try. This match will be full of fun, shot-making, and surprise tactics.
6. Alexander Blockx vs. Alexander Zverev
This match features two players named Alexander who are becoming very familiar with each other. They have already played twice this year in Madrid and Rome, and the German star Alexander Zverev won both times.
The two players had completely opposite experiences at the French Open a few weeks ago. Zverev finally won his very first Grand Slam trophy, proving he is one of the best players in the world. Meanwhile, the 21-year-old Belgian talent, Alexander Blockx, had terrible luck. He slipped on a court cover during practice, hurt his ankle, and has not played a match since. If Blockx’s ankle is fully healed, he has the young energy and talent to upset the champion. However, Zverev enters Wimbledon full of confidence after reaching the semi-finals in Halle.
The Ladies’ Singles: Comebacks, Teenage Dreams, and Reigning Champions
7. Serena Williams vs. Maya Joint
Without a doubt, this is the most talked-about match of the entire first round. The sports world stopped when the draw revealed that Serena Williams is returning to tennis! The 23-time Grand Slam champion has been away from singles tennis for nearly four years.
At 44 years old, Serena enters the tournament as a wild card. Everyone is asking the same question: Can a seven-time Wimbledon winner still dominate the game after so much time away? Her opponent is Maya Joint, a young Australian player who is just starting her journey. Joint has missed a lot of matches in 2026 due to injuries, but she is currently ranked world number 53 and won a grass-court tournament in Eastbourne last summer. This match is pure Hollywood drama—the ultimate veteran queen against a young rising star.
8. Barbora Krejcikova vs. Hannah Klugman
This match is a dream come true for local British fans. Hannah Klugman is a 17-year-old local teenager who just won her first-ever professional WTA match on the grass courts of Nottingham a few weeks ago. Even though she eventually lost to a top-seeded player there, her confidence is sky-high.
However, the teenager has been given the hardest possible draw. She must play Barbora Krejcikova, who won the Wimbledon title in 2024. Krejcikova is known as a “momentum player,” which means that when she starts playing well, she is almost impossible to stop. But if young Klugman can use the loud support of the home crowd and win the first few games, she might be able to create a massive shock.
9. Taylor Townsend vs. Iga Swiatek
Iga Swiatek enters the tournament as the reigning Wimbledon champion and a six-time Grand Slam winner. However, the Polish superstar will have to be alert from the very first point because her opponent plays a very unusual style of tennis.
Taylor Townsend is an American star who is famous for her incredible doubles skills. She plays with her left hand, which makes her shots spin differently, and she loves to rush up to the net to finish points quickly. Swiatek usually prefers to play long rallies from the back of the court. Earlier this week, Swiatek lost a match in Germany to another American, Emma Navarro. Townsend will definitely look at that match to create a blueprint on how to upset the world’s best player.
10. Ashlyn Krueger vs. Donna Vekic
This first-round match features two players who are currently playing the best tennis of their lives. Both are coming into Wimbledon with a lot of wins on grass.
Donna Vekic from Croatia is highly experienced and enters the tournament full of joy. Less than two weeks ago, she won a big trophy at the Queen’s Club in London, even defeating British star Emma Raducanu without losing a single game in the first set. But her opponent, 22-year-old American Ashlyn Krueger, is also on fire. Krueger reached the semi-finals in Birmingham and then won five matches in a row to win a tournament in Ilkley. Because both players have so much confidence on grass, this match will likely come down to just a few important points.
11. Magda Linette vs. Mirra Andreeva
Tennis fans are excited to welcome Mirra Andreeva back to the Grand Slam stage. The incredibly talented teenager just won her very first Grand Slam title at the French Open on clay earlier this month, lifting her up to world number 5.
The big question now is how quickly the young star can adapt her game from the slow red clay of Paris to the lightning-fast green grass of London. It will not be easy. In the first round, she has to play Magda Linette, a tough veteran ranked number 58 in the world. Linette loves Wimbledon and has reached the third round here three times in the past. Andreeva has beaten Linette three times out of their four previous matches, but doing it on grass will be a brand-new challenge for the young Grand Slam champion.
12. Emma Navarro vs. Paula Badosa
This final match features two incredibly talented women who used to be ranked in the top 10 in the world. Both have had a tough time recently but have rediscovered their best form just in time for Wimbledon.
Emma Navarro has had a great grass season, reaching the final in Nottingham and the quarter-finals in Bad Homburg. Paula Badosa has been dealing with a painful leg injury, but she proved she is ready for Wimbledon by defeating top star Coco Gauff in Berlin last week. Badosa leads their head-to-head records with 2 wins to 1, including a victory on grass last summer. This match will be a high-quality physical battle between two players desperate to get back to the top of the tennis world.
Conclusion
Wimbledon 2026 is starting with a bang. Whether you are excited to see Serena Williams step back onto Center Court, eager to watch young teenagers fight for glory, or waiting to see heavy hitters battle it out with big serves, the first round has something for everyone. Make sure to clear your schedule, because these twelve matches promise to deliver unforgettable tennis drama right from day one!