Novak Djokovic leads their head-to-head 12-2 from 14 career meetings with Stefanos Tsitsipas, but none of them have come on grass.

The seven-time Wimbledon champion looked far from his best in a four-set opener against Wu Yibing, while Tsitsipas breezed through Hugo Gaston without facing a single break point.

A coaching split, a ranking at its lowest since 2018, and nothing to lose could make the Greek a dangerous second-round opponent.

• Competition: Wimbledon 2026, Round 2
• Venue: All England Club, London
• Date: Wednesday, July 1, 2026
• Surface: Grass
• Start Time: 1:20 AM AEST

Tsitsipas vs Djokovic Form and Head to Head

Djokovic holds a 12-2 career advantage, though both players will be entering uncharted territory with their first ever meeting on grass.

Their last clash came at the 2024 Paris Olympics quarterfinal, where Djokovic won in straight sets (6-3, 7-6).

That gap of nearly two years adds an element of uncertainty to how this matchup plays out on a surface neither has faced the other on before.

Djokovic’s 2026 season sits at 10-4, highlighted by an Australian Open final appearance against Alcaraz.

His first-round win over Wu Yibing was scratchy, dropping a set and fending off six break points in the fourth set alone across three hours and 12 minutes.

Tsitsipas has had a mixed year results-wise at 16-14, but his 6-1, 6-4, 6-2 demolition of Gaston in round one was clinical. He held serve across all 13 service games without conceding a break point.

New Coach, New Energy for the Greek

Tsitsipas arrived at Wimbledon having split with his father and long-time coach Apostolos just days before the tournament.

He’s now working with Thomas Perrin from the Mouratoglou Academy and has spoken about feeling “free of anxiety and stress” heading into this clash. Whether that translates to sustained performance against a player of Djokovic’s calibre remains to be seen, but the early signs from his opener were encouraging.

Djokovic enters this match with minimal grass-court preparation, playing on the surface for the first time in 2026. This is just his fifth tour-level event of the season, and the rustiness showed against Wu. Both players are fit with no injury concerns reported ahead of Wednesday’s meeting.

Tsitsipas vs Djokovic Betting Markets

The [[match winner market has Djokovic as a heavy favourite, which is no surprise given the lopsided head-to-head and his pedigree at SW19.

Check the latest Tsitsipas vs Djokovic odds for the full range of markets.

You’ll find the full range of markets for this one over at Sportsbet, including set betting and total games options that could offer more value than the outright result.

Set betting is where things get interesting. Tsitsipas’s serving numbers from round one suggest he’s capable of holding firm for stretches, and Djokovic’s vulnerability on return in the Wu match opens the door for at least one competitive set.

Total games could also trend high if Tsitsipas brings the same serving intensity he showed in his opener.

Tsitsipas vs Djokovic Prediction: Our Pick

Djokovic should have too much for Tsitsipas here, but we expect the Greek to pinch a set along the way.

The 12-2 head-to-head record and seven Wimbledon titles tell one story, but the context of this particular match tells another. Djokovic is undercooked on grass, needed three hours and 12 minutes to get past a player ranked outside the top 50, and faces a Tsitsipas who looked sharp and liberated in his opener.

The World No. 87 held serve in all 13 games against Gaston and appears to be playing with renewed freedom following his coaching change.

That said, Djokovic at Wimbledon is a different beast entirely. His ability to raise his level as tournaments progress is well-documented, and he’s historically thrived in matches where he’s been tested early.

We fancy Djokovic to advance, but Tsitsipas looks more than capable of making this a four-set affair. The risk is that Djokovic finds his range early and suffocates Tsitsipas before the Greek can settle, but on balance, the set betting line looks the sharper play alongside the outright result.