Will anyone be eating breakfast at Wimbledon on Friday morning ET, kicking off the sporting action-packed Fourth of July holiday weekend? Relatively unknown and unseeded American Jenson Brooksby could put himself on the world tennis map with an upset victory over world No. 1 and defending champion Jannik Sinner in a match scheduled to start around 9:30 a.m. ET.
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With Sinner at -4500 and Brooksby at +1600, the odds of an upset are obviously incredibly low, but this would be one of the biggest in the sport. The biggest incident on the men’s side at the end of a major that I can remember was at the 2009 French Open, when Robin Soderling defeated defending champion Rafael Nadal in the fourth round, ending Nadal’s 31-match winning streak on clay.
I was actually able to find odds for that fight and Soderling was at +4800. By comparison, Buster Douglas was +4200 when he shocked Mike Tyson in Tokyo in 1990 in what many consider the biggest sporting event upset of a lifetime (myself included).
As far as I can remember, the biggest women’s upset was in the 2015 US Open semifinals, when world No. 1 Serena Williams blew a 2-0 lead in the third set and lost to Roberta Vinci. Serena’s win price was -2000, she was the defending champion and was challenging for a rare calendar year Grand Slam.
So who exactly is Jenson Brooksby? The 25-year-old from Sacramento, California, is ranked 81st in the world, with a career high of 33rd in June 2022. Brooksby’s only title came at the 2025 U.S. Men’s Clay Court Championship, but there were no standouts in that tournament.
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The 6-foot-4 Brooksby, who has autism, went 6-15 in singles at Wimbledon this year, defeating unseeded Aleksandar Vukic in three sets in the first round and then eliminating No. 31 Ignacio Busse 6-2, 6-2, 6-3 in the second round. Simply winning the set on Friday puts Brooksby at +172 and No at -235.
Sinner, on the other hand, remains a -160 favorite to win the tournament, but could be a bit gassed after being drained in two games at the All England Club. He defeated Miomir Kecmanovic in five sets in the first round and Nuno Borges in three sets in the final round, but won two sets in a tiebreak. Borges served at 5-4 in the second set, but Sinner broke for his 95th Grand Slam main draw win, surpassing Nicola Pietrangeli to become the most won by an Italian player.
“I felt like I lacked a lot of games, especially in the first round,” said Sinner, who missed his first grass tournament and looked rusty heading into Wimbledon. “Also, I had some moments (in the second round). I need to get this rhythm back. If you look at the scoreboard, it was very close, so these matches, especially the individual sets, helped me a lot.”
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The only meeting between the two took place on an outdoor hard court in Washington in 2021, with Sinner winning 7-6 (2), 6-1. To win in a straight line here, Sinner is -250. “This is going to be one of the biggest challenges in tennis right now. I love these kinds of challenges. I’ve never doubted my ability to beat any player,” Brooksby said.
Friday will be a busy day for the American men overall in London, with world No. 21 Tommy Paul facing unseeded Hubert Hurkasz of Poland and unseeded Michael Chang facing No. 3 Felix Auger-Aliassime of Canada. The latest odds for an American to win the tournament are +600, with No. 4 Ben Shelton already eliminated.
The remaining top-seeded American is No. 6 Taylor Fritz, who advanced to Round 3 with a straight-sets win over fellow American Patrick Kipson on Thursday. Fritz is +1100 to win Wimbledon and will face unseeded Italian Lorenzo Sonego on Saturday. Fritz opened at -530.
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Brooksby won seven games from Sinner in just two sets in their first matchup, so I absolutely believe they can win at least 11 games in three sets on Friday. My play was Brooksby and I won over 10.5 games at -122 via FanDuel. If you win one tiebreaker, it’s definitely a cash and could go either way (losing 6-4, 6-4, 6-3 works).
