Wimbledon 2026: Top four second-round matches ft. Djokovic vs Tsitsipas

Several Grand Slam champions will be in action in round two of Wimbledon 2026.

Wimbledon continues to deliver high-quality battles as we head into the second round matches. The opening round saw most top seeds advance through, however, there were plenty of thrillers, with both defending champions escaping a tight scare.

A few upsets highlighted the opening round, with fourth seed Ben Shelton losing a five-setter epic, and on the women’s side, Elina Svitolina suffered a shocking straight sets loss.

Let’s now take a look at the four best second-round matches to watch out for at Wimbledon 2026, between July 1 and 2.

4. Jakub Mensik vs Grigor Dimitrov

Roland Garros semi-finalist Jakub Mensik will look to make another deep run at a Grand Slam, and enters the second round after a thrilling five-setter win in the deciding tiebreak over local hope Toby Samuel. The Czech has made a habit of winning intense lengthy battles in Slams, and will hope he has more in the tank for another potential epic.

Grigor Dimitrov was a few games away from stunning World No. 1 Jannik Sinner in the fourth round, leading by 2 sets to none. An unfortunate injury mid-match, forced him to retire, and a long surgery since has kept him away from action for months. The Bulgarian suffered a huge dip in rankings, but his Wimbledon 2026 campaign started off on a promising note, thanks to a straight sets win against Dane Sweeny.

If Dimitrov can continue to serve well, and manage to create inroads on the Czech’s serving, he might have the ability to knock out the 15th seed.

Prediction: Grigor Dimitrov to win in five sets

3. Arthur Fils vs Matteo Berrettini

Arthur Fils has been suffering from injuries for more than a year now, and while he did make the Madrid Open finals, he later went on to withdraw from the Italian Open (mid-match) and the Roland Garros. He returned to action at Wimbledon with a bang, winning in straight sets against Raphael Collignon.

The Frenchman will now take on the big serving Matteo Berrettini, who has had his own share of injury troubles for an extended period of time. The Italian played a tough four setter against Stan Wawrinka, and focus will be on if he can recover in time. Berrettini’s ferocious serve and thunderous forehand, against Fils’ all-round game, form a compelling matchup to look forward to.

Prediction: Arthur Fils to win in four sets

2. Mirra Andreeva vs Barbora Krejcikova

The battle of two Grand Slam champions at Centre Court will be a treat to watch. It is a tough round two match for both players as the in-form and recently crowned maiden Grand Slam champion Mirra Andreeva will take on former SW19 winner Barbora Krejcikova.

Both enter this match with convincing wins under their belt, but have played each other four times in the past, and the Russian has dominated this rivalry, winning their most recent exchange in Ningbo. This is also a rematch of their Wimbledon second-round clash back in 2023, which was also won by Andreeva (6-3 4-0 retired).

Prediction: Mirra Andreeva to win in three sets

1. Novak Djokovic vs Stefanos Tsitsipas

Novak Djokovic survived a stern opening-round examination against Wu Yibing, overcoming the Chinese player 6-4, 5-7, 6-4, 6-4 to extend his flawless first-round record at Wimbledon to 21-0. The seven-time champion was forced to raise his level after dropping the second set and had to save six break points in the fourth before sealing victory in three hours and 11 minutes.

Awaiting him in the second round is familiar rival Stefanos Tsitsipas, who made light work of French qualifier Hugo Gaston with a dominant 6-1, 6-4, 6-2 win to register one of his most convincing performances of the season.

Although Tsitsipas enters the contest with renewed confidence, history overwhelmingly favours Djokovic. The Serbian leads their head-to-head 12-2 and has won each of their last several meetings, including the 2023 Australian Open final.

While Tsitsipas has struggled for consistency over the past year, Djokovic remains one of the strongest grass-court players in history, making this match the most anticipated to battle on Day 3 of Wimbledon.

Prediction: Novak Djokovic to win in straight sets

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