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: Wednesday 7/1
Novak Djokovic vs. Stefanos Tsitsipas: Tsitsipas to win at least one set (-150)
Novak Djokovic is participating in his 21st Wimbledon Championships, and Stefanos Tsitsipas is playing in his ninth. Djokovic has seven Wimbledon titles, and Tsitsipas has never made it past the fourth round at this tournament. While they have very different histories here at Wimbledon, they are very familiar with each other. This will be the 15th match between Djokovic and Tsitsipas. Djokovic holds a 12-2 record against Tsitsipas, and he has won 11 straight against the Greek.
While Djokovic has gotten the better of Tsitsipas, it has not always been easy. These two famously had back-to-back five-setters at Roland-Garros in 2020 and 2021, one of those being a semifinal and the other being a final. Despite the long history between the two, they have never faced off on grass before this. While Djokovic should take care of business for the 12th straight time against Tsitsipas, the Greek should steal at least one set. Djokovic dropped a set to Wu Yibing in the first round at Wimbledon. Tsitsipas should give him a tough challenge as well, even if Djokovic is likely to come out on top.
Iva Jovic vs. Tatjana Maria: Maria +1.5 Sets (-130)
Iva Jovic had a tough start to her clay season. She made a nice run to the semifinals at the Queen’s Club Championships before losing to Emma Raducanu. However, she suffered an injury in that tournament that kept her out for the other Wimbledon precursors she was planning on playing. She was able to get healthy in time for Wimbledon, but her health is still a concern. Jovic is one of the bright young players in the world, but she is still very inexperienced at these Grand Slams. Last year was her first-ever Wimbledon Championships, and she went out in the first round. Tatjana Maria should be able to keep this match close.
Maria is two decades older than Iva Jovic. Jovic had not yet been born when Maria played in her first Wimbledon Championships in 2007. Maria made a magical run to the semifinals here at Wimbledon in 2022, by far the best major run of her career. Maria is playing the best tennis of her life in these closing stages of her career. At 37 years old, she won the 2025 Queen’s Club Championships. That made her the oldest woman to ever win a WTA 500 event. It was also Maria’s first career WTA 500 title. She reached her career-high singles ranking after that victory.
Maria has had another nice grass season in 2026, making the final at the Eastbourne Open in her most recent tournament. Tatjana Maria should win at least one set in this match against the young star, Iva Jovic.
