Wimbledon 2026: Anticipated Matches and Player Highlights

The prestigious Wimbledon tournament begins again Monday in London, with exciting first-round matches in both the men’s and women’s singles brackets. Analysts Ava Wallace, Matthew Futterman, and Charlie Eccleshare offer insights into the draw and share their picks for must-watch matches in the tournament’s opening days.

Serena Williams’ Return to Singles

Serena Williams returns to singles play with a favorable first-round draw. At 44, with 23 Grand Slam singles titles, Williams faces Maya Joint, a 20-year-old Australian who has struggled this season. Joint, from Michigan, is a former Eastbourne Open winner but has not performed well in 2026.

If Williams advances, she is likely to face 21-year-old Alexandra Eala of the Philippines in the second round. Eala has shown strong grass-court performances recently, defeating notable players like Donna Vekić and Elena Rybakina. A potential third-round match with defending champion Iga Świątek could await if Williams progresses.

In doubles, Serena pairs with her sister Venus Williams. They will compete against Colombia’s Camila Osorio and Argentina’s Solana Sierra, neither being doubles specialists.

Jannik Sinner’s Path

Jannik Sinner looks to advance deep into the men’s singles competition. His primary challenge might be Novak Djokovic, a seven-time Wimbledon champion. Sinner lost at the French Open due to illness and heat despite a strong start against Juan Manuel Cerúndolo.

Potential quarterfinal or semifinal challenges include Daniil Medvedev and other contenders. However, Sinner’s draw appears clear of significant early threats, similar to last year’s unexpected challenge faced by Carlos Alcaraz.

Matches to Watch: Matt Futterman

• Bianca Andreescu (Q) vs. Zhang Shuai
• Serena Williams (WC) vs. Maya Joint
• Hugo Gaston (Q) vs. Stefanos Tsitsipas
• Alexander Blockx vs. Alexander Zverev (2)

Top American Women at Wimbledon

American players have reasons to celebrate as July 4 coincides with Wimbledon. Top-seeded Jessica Pegula, Amanda Anisimova, and Coco Gauff enjoy promising early-round draws, crucial for building momentum on grass courts.

Pegula, ranked No. 4, has focused on conditioning over playing pre-tournament events. She might encounter fellow American Iva Jovic in the fourth round and Gauff in the quarterfinals. Gauff’s potential fourth-round opponent could be Belinda Bencic. Anisimova might face a third-round challenge from Madison Keys and a possible quarterfinal against Elena Rybakina.

Coco Gauff seeks her first grass-court match win since 2024, providing added motivation.

Novak Djokovic’s Grand Slam Quest

Novak Djokovic faces an uphill path for his 25th Grand Slam title. Sharing the spotlight with Serena Williams may ease media pressure, yet he remains concerned with his challenging draw. Like in the French Open, his stamina over long matches is crucial.

Djokovic’s potential fourth-round opponents include Andrey Rublev or Joao Fonseca, who defeated Djokovic at the French Open. A quarterfinal could feature Félix Auger-Aliassime, eager to capitalize on past missed opportunities.

Matches to Watch: Ava Wallace

• Jeļena Ostapenko vs. Harriet Dart (WC)
• Emma Navarro (23) vs. Paula Badosa
• Marin Čilić vs. Daniil Medvedev (8)
• Frances Tiafoe (17) vs. Térence Atmane

Challenges for Women’s Favorites

Top women’s players face tough early challengers. Defending champion Iga Świątek opens against Taylor Townsend, a skilled doubles and net player. Potential later rounds might pit her against Serena Williams, Alexandra Eala, or Tereza Valentová.

Mirra Andreeva begins against seasoned player Magda Linette, with a second-round matchup possible against former champion Barbora Krejčíková. Aryna Sabalenka, seeded world No. 1, enters against qualifier Teodora Kostović and could face other formidable opponents, including Emma Raducanu or Jeļena Ostapenko.

Sabalenka might benefit from facing strong opponents early, helping her focus and perform better.

A Competitive Men’s Draw

The men’s fourth quarter presents heavyweight matchups. Taylor Fritz faces Jack Draper in a challenging first round. With both having faced injury setbacks, this promises intense competition.

Frances Tiafoe, fresh from a title win, anticipates matches with Alexander Bublik and potentially Jiří Lehečka and Francisco Cerúndolo. Notably, Alexander Zverev, the French Open champion, confronts strong contenders, including Alexander Blockx and other dangerous unseeded players.

Matches to Watch: Charlie Eccleshare

• Yulia Putintseva vs. Tatjana Maria
• Taylor Townsend vs. Iga Świątek (3)
• Stan Wawrinka (WC) vs. Matteo Berrettini
• Taylor Fritz (6) vs. Jack Draper

What matchups are you anticipating most? Share your thoughts in the comments.