Five eye-catching first-round matches at Wimbledon 2026: Serena Williams, Jannik Sinner and more

Wimbledon 2026 commences in only three days, spanning from June 29 to July 12.

The draw for both the gentlemen's and women's tournament was drawn on Friday, June 26 – and it has produced the possibility of some blockbuster showdowns and surprise exits. 

Here, Sports News Blitz writer Jack George highlights the fixtures you won't want to miss.

Jannik Sinner faces Miomir Kecmanović

Reigning Wimbledon champion and world number one Jannik Sinner is to play Serbian Miomir Kecmanović in the first round of the tournament.

Kecmanović relies on excellent rally tolerance to break down opponents and is exceptionally good at covering the whole court.

If the conditions are as hot as in Roland Garros, which saw Sinner lose in the round of 64, Kecmanović’s skills could be an advantage in an attempt to cause an upset.

However, given Sinner's record at Wimbledon, a 20-4 win loss record, he should breeze past the first round.

The Italian has been drawn on the same side of the tournament as Serbian great Novak Djokovic and Russian Daniil Medvedev.

This means it's likely Sinner will face Medvedev in the quarter-finals and Djokovic in the semi-finals of the tournament.

This sets up the possibility of a blockbuster showdown between two of the best.

READ MORE: Wimbledon 2026 preview: Jannik Sinner's title defence, Williams sisters' return and more

Brit Jack Draper faces tricky first round

Jack Draper faces sixth-seed Taylor Fritz in the first round of Wimbledon.

This is an extremely tough fixture, especially given the fact Draper has just returned from an injury-ridden 11-month period, dealing a slight blow to hopes of a positive run.

Britain’s hometown hero, whose best result at Wimbledon is the second round, will be hoping he can cause an upset and get much further into the tournament.

Draper’s recent positive performances in the Eastbourne Open bode well.

He has reached the semi-finals and will play Frenchman Ugo Humbert on Friday.

American Fritz comes into Wimbledon high in confidence having recently beaten Alexander Zverev and Ben Shelton, who both rank higher than himself, in the ATP Halle tournament.

Serena Williams has hopes boosted 

All-time great Serena Williams returns to Wimbledon for the first time since 2022 through a wildcard.

She has won this historic tournament seven times.

Williams’ hopes of a positive return to Wimbledon were boosted when she was drawn against unseeded Australian Maya Joint, who is 20 years old.

Joint’s best result at Wimbledon is a first-round exit in 2025, her only appearance of her career.

This match will be a prime example of experience against youth.

Williams will definitely fancy her chances of advancing into the second round - and she will also feature in the doubles tournament alongside sister Venus Williams.

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Emma Raducanu hopes for more positive Wimbledon

Emma Raducanu, who hasn't really found her form again since her illustrious US Open victory, will be hoping she can go far this year.

At Wimbledon 2025, Raducanu played very well - however, she had to face world number one Aryna Sabalenka in the third round and ultimately lost despite playing very competitively. 

Raducanu will play Croatian Antonia Ružić in the first round of the 2026 tournament - and Ružić has only ever played in the first round at Wimbledon.

Raducanu comes off the back of a positive London performance, in which she lost in the final at Queen’s.

This is certainly a winnable fixture for Raducanu.

Other Brits playing in the first round are: Cameron Norrie who faces qualifier Zheng and Katie Boulter who faces Italian qualifier Tyra Grant.

Djokovic begins hunt for record 25th Grand Slam title

Djokovic, 39, will face Yibing Wu in the first round of the competition.

Wu is ranked 99th in the world, compared to Djokovic’s ranking of eighth.

Djokovic is expected to breeze past Wu and advance further into the tournament.

The Serbian great will have to beat Sinner in the semi-finals, if they both reach that stage, in order to get into the final.

This is a tall order given the fact Sinner has been remarkable all season and quite noticeably better than the rest.

However, Djokovic has beaten Sinner before and it's not wise to rule out a 24-time Grand Slam champion.

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