It's tough to address Wimbledon in this space because the matches start early Eastern time, but I do want to look at Wednesday's second-round men's singles match between No. 7 Novak Djokovic and unseeded but former world No. 3 Stefanos Tsitsipas. It's one of the marquee second-round matches at the All England Club on Wednesday morning Eastern time and played on Centre Court.
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Djokovic is looking for career Grand Slam title No. 25, which would break a tie with female record-holder Margaret Court for the most in history. The 39-year-old Serb has won seven Wimbledon titles, one shy of Roger Federer's all-time mark. Djokovic is the +700 second favorite to win the tournament, behind world No. 1 Jannik Sinner, and not only do I not give Djokovic much of a chance at the title in perhaps his final Wimbledon, but I believe he might be upset by Tsitsipas.
In his first-round match, Djokovic looked quite average in a four-set victory over China's unseeded Yibing Wu, 6-4, 5-7, 6-4, 6-4. Djokovic had to fend off six break points in the fourth set, including three from down 40-love at 2-3 to avoid a major upset vs. the world No. 102. Djokovic improved to 21-0 in Wimbledon first rounds on Monday, and it came one month to the day after he blew a two-set lead over Joao Fonseca at the French Open to lose in five.
I just wonder how much he has in the tank after being out there for 3½ hours Monday with celebrities such as David Beckham and Bad Bunny watching the match vs. Wu. It was Djokovic's first time playing on grass this year, and only his fifth Tour-level event, so he's not in the best of condition.
"He put me under a lot of pressure," Djokovic said of Wu. "I was lucky he missed the overhead and break point, and I probably should have lost that fourth set as he had many break points. These kind of matches are decided in a few points. Fortunately, I have the experience of 20 years to manage this kind of situation."
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Greece's Tsitsipas once was a top 10 mainstay in the ATP world rankings and owns 12 career titles, but the 27-year-old is down at No. 87 in the world, his lowest ranking since January 2018, due to inconsistent play – he retired in the first round at Wimbledon last year – and injuries.
At one point, Tsitsipas was hailed as a future star and one of the next "Big Three" along with Alexander Zverev and Daniil Medvedev set to take over men's tennis eventually from Roger Federer, Rafael Nadal and Djokovic. But Tsitsipas hasn't sniffed a major title since losing in the 2023 Australian Open final to Djokovic in three sets (two tiebreakers).
Ahead of this year's Wimbledon, Tsitsipas fired his father Apostolos Tsitsipas as his coach for a second time and began working with Frenchmen Thomas Perrin and Patrick Mouratoglou. So far, so good as Tsitsipas easily won his first-round match against France's Hugo Gaston on Monday, 6-1, 6-4, 6-2, barely breaking a sweat.
"Let me start by saying that I'm missing the way I have been playing the last couple of years," Tsitsipas said. "Regardless of the result, I always felt like I was coming into this tournament with a lot of determination, with a lot of love for the grass, and always played my best that I knew at the time."
This will be the 15th all-time meeting between Tsitsipas and Djokovic, with the latter winning 12. But almost impossibly, they have never met on grass. The last win for Tsitsipas in the series was on the outdoor hard courts of Shanghai in 2019. Their last meeting was on the clay of Roland Garros at the 2024 Paris Olympics, and Djokovic won in two sets.
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The 6-foot-4 Tsitsipas can hit as big as anyone, winning 77% of first serves this season, and appears to have some confidence back and is only 27. Thus, I think he can get at least a set Wednesday, if not threaten an upset, so I'm on the Greek +2.5 sets at -150.
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