Stefanos Tsitsipas vs. Novak Djokovic Prediction, Odds for Wimbledon Second Round

Novak Djokovic is through to the second round at Wimbledon, and he has a familiar foe on deck in the second round on Wednesday.

Stefanos Tsitsipas cruised past Hugo Gaston in the first round, reaching the second round at the All England Lawn Tennis and Croquet Club for just the fifth time in his career.

There is a lengthy history between these two players, as they’ve matched up 14 times overall and three times in a Grand Slam. They’ve never shared the court at Wimbledon, making Wednesday’s match one of the top ones to watch.

Djokovic is favored to advance, but after a shaky French Open showing – he was knocked out in the third round – the legend isn’t as big of a favorite as you’d expect considering he’s won every match against Tsitsipas since 2020.

Let’s take a look at the odds, each player’s history at Wimbledon and my prediction for this second-round showdown.

Stefanos Tsitsipas vs. Novak Djokovic Odds and Total

Odds via DraftKings Sportsbook

Moneyline

Stefanos Tsitsipas: +482
Novak Djokovic: -760

Total

37.5 (Over -115/Under -125)

Stefanos Tsitsipas vs. Novak Djokovic How to Watch

Date: Wednesday, July 1
Time: 12:00 p.m. EST
How to Watch (TV): ESPN/ESPN Unlimited

Stefanos Tsitsipas vs. Novak Djokovic History and Wimbledon Performance

Stefanos Tsitsipas

Tsitsipas has struggled to find his peak form in recent years, failing to reach the third round of a Grand Slam in 2025 and so far in 2026.

His last run past the second round came in the 2024 French Open, and he hasn’t been great at Wimbledon, losing in the first round four times. He knocked off Hugo Gaston in Round 1, winning 6-1, 6-4, 6-2.

Novak Djokovic

Djokovic is a legend, and he’s already won at the All England Lawn Tennis and Croquet Club seven times in his career. The last time the 39-year-old won at Wimbledon was in 2022, though he was the runner-up in 2023 and 2024 before losing in the semifinals in 2025.

He has a lengthy history against Tsitsipas, going 12-2 against him in 14 meetings. Djokovic has won the last 11 head-to-head matchups, though they have not faced off since 2024.

In Round 1, Djokovic needed four sets to take down Yibing Wu, winning 6-4, 7-5, 6-4, 6-4.

Stefanos Tsitsipas vs. Novak Djokovic Prediction and Pick

Djokovic has dominated Tsitsipas in the past, winning 12 of their 14 previous matchups, but the 39-year-old dropped a set in Round 1 and didn’t exactly have his best showing at the French Open.

Djokovic dropped at least one set in each of those matches, so I don’t think it’s crazy to bet on Tsitsipas to win at least one set on Wednesday.

Tsitsipas hasn’t made it out of the second round in a Grand Slam since the 2024 French Open and both of his wins against Djokovic came prior to 2020. So, I don’t expect an upset, even though I think Tsitsipas can steal a set.

These two haven’t matched up since the 2024 Olympics, so looking at past results isn’t exactly super indicative of Djokovic’s play as of late. The legend should advance, but I wouldn’t be shocked if drops another set like he did to Yibing Wu.

Pick: Stefanos Tsitsipas +2.5 Sets (-150 at DraftKings)

Odds refresh periodically and are subject to change.

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