Anyone for Breakfast at Wimbledon on Friday morning Eastern time to kick off a July 4 holiday weekend chock-full of sports action? Relative unknown and unseeded American Jenson Brooksby could put himself on the worldwide tennis map with an upset of No. 1 and defending champion Jannik Sinner of Italy in a match with an expected start time around 9:30 a.m. ET. New bettors interested in wagering on tennis need to check out the recent BetMGM promo code.
An upset obviously is incredibly unlikely, with Sinner at -4500 and Brooksby at +1600, but this would rank as one of the biggest in the sport. The biggest on the men’s side I can recall in the later stages of a major was at the 2009 French Open, when Robin Soderling knocked off four-time defending champion Rafael Nadal in the fourth round, ending Nadal’s 31-match clay winning streak.
I was actually able to find odds on that match, and Soderling was +4800. By comparison, in what many consider to be the single biggest sporting event upset of their lifetimes (as I do), Buster Douglas was +4200 when he shocked Mike Tyson in Tokyo in 1990.
As for the biggest women’s upset, from what I can remember, it would be when world No. 1 Serena Williams was beaten by Roberta Vinci in the 2015 U.S. Open semifinals, blowing a 2-0 lead in the third set. Serena was priced -2000 to win, was the defending champion and going for the rare calendar-year Grand Slam.
So who exactly is Jenson Brooksby? The 25-year-old from Sacramento, Calif., is ranked No. 81 in the world with a career-best mark of No. 33 in June 2022. Brooksby’s lone title came at the 2025 U.S. Men’s Clay Court Championships, which didn’t have a stellar field.
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The 6-foot-4 Brooksby, who deals with autism, entered Wimbledon just 6-15 in singles this year but took out unseeded Aleksandar Vukic in three sets in Round 1 and then routed No. 31 Ignacio Buse 6-2, 6-2, 6-3 in Round 2. Simply to win a set on Friday, Brooksby is +172, with No at -235.
Sinner, meanwhile, remains the -160 tournament favorite but could be a bit gassed after two draining matches at the All England Club. He beat Miomir Kecmanovic in five sets in the first round and then Nuno Borges in three sets in the last round but two in tiebreakers. Borges served for the second set at 5-4, but Sinner broke and earned his 95th career main-draw win at a Grand Slam event to move past Nicola Pietrangeli for the most by an Italian player.
“Especially in the first round, I felt the lack of matches,” mentioned Sinner, who for the first time did not play a grass tournament in the lead-up to Wimbledon and has looked rusty. “Also [in Round 2] there were a couple of moments. I need to get back to this rhythm. If we look at the scoreboard, it was very close, so these matches, and especially the individual sets, help me a lot.”
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The lone matchup between these two previously came in 2021, on the outdoor hardcourts in Washington, and Sinner won 7-6(2), 6-1. To win in straight sets here, Sinner is -250. “It will be one of the biggest challenges in tennis right now. I love these kinds of challenges. I never doubt my ability to beat any player,” Brooksby mentioned.
Friday is a busy day for American men overall in London, as No. 21 Tommy Paul faces unseeded Hubert Hurkacz of Poland, and unseeded Michael Zhang meets No. 3 Felix Auger-Aliassime of Canada. The updated odds for an American man to win the tournament – with No. 4 Ben Shelton already out – is +600.
The top-seeded USA male remaining is No. 6 Taylor Fritz, who advanced to Round 3 with a straight-sets win Thursday over fellow American Patrick Kypson. Fritz is +1100 to win Wimbledon and faces unseeded Italian Lorenzo Sonego on Saturday. Fritz opened at -530.
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Brooksby got seven games off Sinner in their first meeting in only two sets, so I absolutely think he can get at least 11 games in three sets Friday. My play is Brooksby Over 10.5 games won at -122 via FanDuel. If we get one tiebreaker, that’s surely cashing and may anyways (6-4, 6-4, 6-3 loss works).
