The third major of the tennis season is here! Anything can happen at Wimbledon, and there is bound to be a couple of big upsets in this first round.
These are my 2026 Wimbledon best bets to target on DraftKings Sportsbook for the first round of the tournament.
2026 Wimbledon Best Bets: Monday 6/29
Jan-Lennard Struff vs. Sebastian Baez: Struff -1.5 Sets (-130)
Jan-Lennard Struff should handle Sebastian Baez in this opening round match. Struff has made the third round at Wimbledon each of the past two years, which included an upset of Felix Auger-Aliassime last year. Struff is a very experienced player and has a lot of majors under his belt. While it was in doubles, not singles, Struff did just win a title in Stuttgart a few weeks ago on grass. That should have given him some good confidence heading into Wimbledon.
Sebastian Baez has only won one match in four career Wimbledon Championships main draws. Baez is a clay specialist, with 10 of his 12 career ATP Tour finals coming on clay, and the other two coming on hardcourt. All 10 of his Challenger Tour finals have come on clay as well. Baez has never found much success on grass and is unlikely to be very competitive in this match. Struff should take care of business in three or four sets.
2026 Wimbledon Best Bets: Tuesday 6/30
Taylor Fritz vs. Jack Draper: Fritz to win 3:2 (+380)
Taylor Fritz and Jack Draper face off in one of the biggest first-round matches in recent memory. At their best, these are two of the top players in the world. However, they have both struggled with injuries in 2026. That has been the story of Draper’s career, unfortunately. After missing the end of last year and the beginning of this year through injury, it looked like Draper was back when he defeated Novak Djokovic at Indian Wells. However, it wasn’t long before Draper suffered another injury. He finally made his return at Eastbourne to prepare for Wimbledon, where he made the semi-finals.
Fritz has also struggled with both injuries and form this year. However, he too had a good lead-up to Wimbledon by making the final in the Terra Wortmann Open. Fritz was a semi-finalist at Wimbledon last year and would love to make another deep run in the tournament. However, this is a very tough opening-round opponent. I am backing Fritz to win, but it could go all the way to the brink. At odds of +380, I love this bet on Fritz to win in five sets.
Fritz was pushed to five sets in the first round at Wimbledon last year. Draper and Fritz have also played tight matches over the years. Draper has won three of the five career meetings between them. However, three of the past four meetings have been three-setters at non-majors. Fritz’s serve should give the lefty a lot of trouble on this surface. However, Draper, with the home crowd at his back, will be a serious threat. There is a lot of value in this bet, and it seems like a real possibility with the way these two match up.
Serena Williams vs. Maya Joint: Williams ML (+118)
Serena Williams is making her triumphant return to professional tennis at Wimbledon in 2026. Williams is the greatest player in the history of the women’s game. She has 23 Grand Slam singles titles, the most in the Open Era. She won seven of those major titles at Wimbledon, tied with the Australian Open for her most successful Grand Slam venue. However, the 44-year-old has not played competitive tennis in a long time. Williams has not played at a major since the 2022 US Open.
On June 9, 2026, Williams made her first professional appearance in 1,375 days by competing in doubles at the Queen’s Club Championship. Alongside Victoria Mboko, Williams made the quarter-finals before the team had to withdraw due to an injury to Mboko. While it was doubles, Williams proved she could still compete at a professional level. Williams then announced that she would be playing doubles at Wimbledon, alongside her sister Venus. The duo has won six doubles titles at Wimbledon over the years. However, the real shock came once Williams announced she would be playing singles as well.
Williams is facing 20-year-old Australian Maya Joint in the first round at Wimbledon. Joint is currently the No. 53 player in the world, but has won just two main draw matches at majors in her career, neither of which came at Wimbledon. By the time Joint was born, Serena Williams had already won two Wimbledon titles. While it’s unclear how ready Williams is for high-level singles tennis, this moment might be too big for Joint. There will be a lot of press and a wild crowd around this match. Williams is the greatest of all time, and Joint has never had success at this high a level. Serena Williams might not be the Serena Williams of old, but she has enough in the tank to pull off the upset and win a match at Wimbledon.
