The third major of the tennis season is here! Anything can happen at Wimbledon, and the first round already saw some big upsets.
These are my 2026 Wimbledon best bets to target on DraftKings Sportsbook for the second round of the tournament.
2026 Wimbledon Best Bets: Thursday 7/2
Parlay (-115): Iga Swiatek ML (-396) & Amanda Anisimova to win 2:0 (-200)
The first leg of this parlay is Iga Swiatek on the Moneyline against Karolina Pliskova. Swiatek had a tough first-round matchup against Taylor Townsend, but she took care of business. Swiatek is the defending champion here at Wimbledon and should go on another deep run. She has not had her best form in 2026, but she should survive this match. Pliskova had an incredible run to the 2021 Wimbledon final, but she has not made it past the second round since then. Iga Swiatek has won five straight matches against Pliskova, including earlier this year at Indian Wells. Swiatek should handle business and move on to the third round.
Amanda Anisimova was the runner-up to Iga Swiatek at last year’s Wimbledon final, so it’s fitting to pair them in this parlay. Just like Swiatek, Anisimova has not played her best tennis in 2026. However, she looked dominant in her first-round matchup against Lina Gjorcheska. Perhaps Anisimova needed to return to the site of her first major final to find her form again. She should have a convincing win against Sofia Kenin. In six trips to Wimbledon, Kenin has only made the third round once. Anisimova should take Kenin down in two sets in this match.
Arthur Fils vs. Matteo Berrettini: Over 39.5 Total Games (-125)
Arthur Fils has had a disappointing summer. The 22-year-old Frenchman looked like one of the next big things on the ATP Tour earlier this year. He made the final in Qatar, the quarters in Indian Wells and the semis in Miami. Fils followed up that run of success by winning the title in Barcelona, then making the semis in Madrid. Unfortunately, that is when the injuries struck. He missed the rest of the clay season, including Roland-Garros. Fils returned just in time for Wimbledon. Fils missed Wimbledon through injury last year, but he made the fourth round in 2024, his best-ever major finish.
Fils will be taking on Matteo Berrettini, who is trying to jumpstart his career after dealing with his own injuries the past few years. Berrettini made the final here at Wimbledon back in 2021, just before the injuries started to pile up for him. Berrettini made it back to a major quarterfinal for the first time since Wimbledon 2021 at Roland-Garros earlier this summer. He is trying to take advantage of this healthy period of his career and make more deep runs at Grand Slams.
This should be a great match between these two players. Fils is the rising star, trying to get back to the top level that he was at earlier this season. Meanwhile, Berrettini is the aging player trying to get the last juice out of his career. These two should compete hard and could push this match to five sets.
