It’s hard to talk about Wimbledon in this area since the matches start early ET, but I’d like to focus on Wednesday’s second-round men’s singles match between world No. 7 Novak Djokovic and unseeded former world No. 3 Stefanos Tsitsipas. It was one of two high-profile second-round matches to be played at the All England Club on Wednesday morning ET on Center Court.
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Djokovic is aiming for her 25th Grand Slam title, breaking the all-time tie with women’s record holder Margaret Court. The 39-year-old Serbian has won Wimbledon seven times, just one shy of Roger Federer’s all-time record. Djokovic is the +700 second favorite to win the tournament, behind world No. 1 Jannik Sinner, which I believe not only doesn’t give Djokovic much of a chance to win the title, likely at last Wimbledon, but he may be upset by Tsitsipas.
Djokovic looked pretty ordinary in the first round, winning in four sets over unseeded Wu Yibin of China 6-4, 5-7, 6-4, 6-4. Djokovic had to avoid six break points, including three from 40 love down 2-3 in the fourth set, to avoid a major upset against the world No. 102. Djokovic improved to 21-0 in the first round of Wimbledon on Monday, a month after blowing a two-set lead to defeat Joao Fonseca in five at the French Open.
It will be interesting to see how much he has left in the tank after being out for three and a half hours watching the game against Woo with celebrities like David Beckham and Bad Bunny on Monday. This is Djokovic’s first time playing on grass this year and only his fifth tour-level event, so the conditions aren’t the best.
“He put a lot of pressure on me,” Djokovic said of Wu. “I was lucky that he missed an overhead and a break point. He had a lot of break points and I probably should have lost the fourth set. These kinds of matches are decided by a few points. Fortunately, I have 20 years of experience in dealing with these kinds of situations.”
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Greece’s Tsitsipas was once a top-10 mainstay in the ATP World Rankings and owns 12 career titles, but inconsistent play (he withdrew in the first round at last year’s Wimbledon) and injuries have left the 27-year-old languishing at No. 87 in the world rankings, his lowest since January 2018.
At one point, Tsitsipas was hailed as a future star, one of the next “big three” along with Alexander Zverev and Daniil Medvedev who were set to eventually take over men’s tennis from Roger Federer, Rafael Nadal and Djokovic. However, Tsitsipas has not sniffed a major title since losing to Djokovic in three sets (two tiebreaks) in the 2023 Australian Open final.
Ahead of this year’s Wimbledon, Tsitsipas sacked his father Apostolos Tsitsipas as coach for the second time and began working with Frenchmen Thomas Perrin and Patrick Mouratoglou. So far, Tsitsipas has been in such good form that he easily won his first round match against France’s Hugo Gaston on Monday, 6-1, 6-4, 6-2, barely breaking a sweat.
“First of all, I’ll say that I miss the way I played over the last few years,” Tsitsipas said. “Regardless of the result, I always felt like I went into this tournament with a lot of determination and a love for the grass, and I always played the best I knew how to play at the time.”
This is the 15th time Tsitsipas and Djokovic have played against each other, with Djokovic winning 12 times. But, almost improbably, the two have never faced each other on grass. Tsitsipas’ last victory in the series came in 2019 on an outdoor hard court in Shanghai. Their last meeting was on clay at Roland Garros at the 2024 Paris Olympics, with Djokovic winning in two sets.
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At 6-foot-4, Tsitsipas can hit as big as anyone, winning 77 percent of his first serves this season and appears to be regaining some confidence, but he’s still just 27 years old. So I’m taking Greece +2.5 sets at -150 because I think they can at least win a set on Wednesday, even if there’s no threat of an upset.
