Grigor Dimitrov almost made some serious history last year at Wimbledon.
The Bulgarian was up two sets to love on Jannik Sinner, and he had the Italian on the ropes in the third set. The tennis gods would not allow the upset, though, as Dimitrov injured himself during a point and had to retire from the match.
Sinner would go on to win the title.
It was a microcosm of Dimtrov’s career.
Considered one of the best players of this generation to never win a Grand Slam, Dimitrov is back at Wimbledon as a wild card entry as he tries to sort his way through an inconsistent campaign.
He’ll get Centre Court treatment for his match against Jakub Mensik on Thursday afternoon. The Czech is a -184 favorite to get through Dimitrov.
Wimbledon: Dimitrov vs. Mensik pick
At his best, Dimitrov is a five-tool player. He can move gracefully, he’s got incredible touch around the net, and he’s got a terrific serve. Unfortunately, his best days are way behind him. Age and injuries have caught up to the 35-year-old.
That said, he’s not without a chance against Mensik.
After making it to the semifinals on the clay at Roland Garros, Mensik is now on a surface that he hasn’t quite figured out. The 20-year-old is 6-9 in his career on grass, and he just needed a fifth-set tiebreaker to get by World No. 123 Toby Samuel in Round 1.
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Mensik lost his only warmup match on the grass to Adrian Mannarino.
Dimitrov wasn’t 100 percent crisp in his Round 1 win over World No. 123 Dane Sweeny, but he still managed to get through the Aussie in straight sets.
Critically, this is a surface that Dimitrov has always loved. His speed, touch, and power make him a real chore on the lawn.
With the crowd behind him and an unsure opponent in front of him, Dimitrov has value to pull the upset on Thursday.
The Play: Dimitrov moneyline (+152, FanDuel)
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Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.















