Wimbledon 2026: Top five first-round matches to watch out for at SW19

From Draper’s return to Wawrinka’s emotional farewell, Wimbledon 2026 kicks off with thrilling first-round matchups.

Wimbledon has a history of delivering top-quality battles right from the opening rounds. With nine different women’s singles champions in the last nine editions, the tournament has become a testament to its unpredictability.

The 2026 Championships will once again feature several highly anticipated first-round clashes involving top-ranked players, emerging talents, and former champions whose rankings no longer reflect their true ability.

On that note, let’s take a look at the five best first-round matches to watch out for at Wimbledon 2026, between June 29 and 30.

5. Emma Navarro vs Paula Badosa

A blockbuster opening round awaits between two players who were formerly in the top-10 rankings. Emma Navarro arrives on the back of a superb grass season, having reached the final of Nottingham Open. The American also recently outclassed Wimbledon champion Iga Swiatek in the Bad Homburg competition, and will be full of confidence.

Paula Badosa, meanwhile, is trying to return to winning ways after a long battle with injuries. The Spaniard showed glimpses of her best form when she beat Coco Gauff in Berlin, with the question being if she can continue to sustain that level. Badosa holds a 2-1 head-to-head lead over Navarro, with their most recent exchange ending with a win for the Spaniard in Berlin last year.

Prediction: Emma Navarro to win in three sets

4. Matteo Berrettini vs Stan Wawrinka

Matteo Berrettini begins his Wimbledon 2026 campaign against three-time Grand Slam champion Stan Wawrinka in a clash between two of the tour’s biggest hitters.

While Wawrinka still possesses the firepower to trouble any opponent on his day, the 41-year-old has struggled for consistency, losing eight of his last ten matches and exiting in the first round of four of his last five Grand Slam appearances. Given that this will be his last appearance on a grass court, expect the Swiss to give everything he has on court.

Berrettini, a former finalist here, arrives after a quarter-final run at Roland Garros and, provided he has fully recovered from the injury that forced his retirement in Paris, remains one of the most dangerous players on grass.

Prediction: Matteo Berrettini to win in five sets

3. Serena Williams vs Maya Joint

Serena Williams returns to Wimbledon singles competition for the first time since the 2022 US Open, taking on Australia’s Maya Joint in one of the most anticipated first-round matches of the Championships. The 23-time Grand Slam champion enters the tournament on a wildcard after nearly four years away from singles tennis.

Although she featured in doubles events at Queen’s Club and Berlin in the lead-up to Wimbledon, this will be her first singles match since her comeback. Joint, meanwhile, has endured a difficult 2026 season, winning just three matches and arriving on the back of nine defeats in her last ten outings.

Despite the long layoff and understandable concerns over Serena’s match fitness at 44 years of age, Wimbledon has always been her most successful stage, where she has lifted the trophy seven times. Her experience, elite serve and ability to raise her level on the biggest occasions could prove decisive against an opponent struggling for confidence.

Prediction: Serena Williams to win in three sets

2. Marin Cilic vs Daniil Medvedev

Another interesting R1 clash pits two former Grand Slam winners together. Daniil Medvedev has not enjoyed a great run in Grand Slams since 2025, including a defeat in the opening round last year at SW19. The Russian had reached consecutive semi-finals in this competition prior to that, but his form in recent times hasn’t been reliable.

Marin Cilic, on the other hand, arrives after managing just three wins in the 2026 grass season, which includes a defeat at the hands of Medvedev in Halle. The Russian should be able to repeat his heroics, but Cilic’s big serving and Medvedev’s unorthodox play make this a must-watch contest.

Prediction: Daniil Medvedev to win in four sets

1. Taylor Fritz vs Jack Draper

A high-quality opening round awaits as two sensational ATP talents are set to clash. Only one of Taylor Fritz and Jack Draper will advance to the second round, which is unfortunate. However, the Brit’s longtime absence from the tour led to a decline in his rankings, and he enters the event as an unseeded player.

Draper played a couple of grass-court events ahead of Wimbledon, having reached the semi-finals in Eastbourne. Fritz, on the other hand, reached the finals at both Stuttgart and Halle. The American had also finished as a semi-finalist in SW19 last year, and pushed Carlos Alcaraz to the limit.

He now has a superb chance to reach the final, as he avoids both Novak Djokovic and Jannik Sinner in his draw, but will look to first settle scores against the local hope, against whom he trails 2-3 in the head-to-head.

Prediction: Taylor Fritz to win in five sets

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