The 2025 Wimbledon Championships kicked off on Monday, June 30, with first-round matches in both the men’s and women’s singles. Day one of the grass-court Major saw quite a few upsets, as the No. 9 seed in the men’s draw and the No. 20 seed in the women’s draw were eliminated. With that in mind, let’s take a look at the biggest shock upsets from Day 1 of Wimbledon 2025.
7 Shocking Upsets in First Round of Wimbledon 2025
#7 Jelena Ostapenko
One of the upsets on the first day of the women’s singles event at Wimbledon came when 20th seed Jelena Ostapenko of Latvia was knocked out by Sonay Kartal. Ostapenko fell to the World No. 51 in a hard-fought three-set match, taking only the second set. Kartal triumphed with a final score of 7-5, 2-6, 6-2.
In 2024, Ostapenko reached the quarterfinals of the grass-court Slam, where she was defeated in straight sets by Barbora Krejčíková. Her best run at the tournament came in 2018, when she advanced to the semifinals, where she fell in straight sets to Angelique Kerber. Kartal will now take on Bulgarian Viktoriya Tomova in the second round.
#6 Daniil Medvedev
On the men’s side, ninth seed Daniil Medvedev made a shock exit in the first round, losing to Benjamin Bonzi. The 64th-ranked Frenchman defeated the Russian in a hard-fought four-set battle. Medvedev managed to win only the second set, with the final score reading 6-7(2), 6-3, 6-7(3), 2-6.
This marks a first-round exit for Medvedev, who reached the last-four stage at the All England Club in the past two years, where he lost both times to World No. 2 Carlos Alcaraz. In the second round, Bonzi will face Australian Jordan Thompson on Wednesday.
#5 Ons Jabeur
30-year-old Tunisian and former world No. 2 Ons Jabeur made an early exit from the tournament after being forced to retire during her opening match. The two-time tournament finalist was up against Bulgaria’s Viktoriya Tomova, but the match took a concerning turn midway through the first set. Jabeur took a lengthy 14-minute medical timeout.
After the medical timeout, the Tunisian returned to the match and managed to force a tiebreak to decide the first set. She led 5-4 in the breaker, but Tomova came back to take it 7-5. Just two games later, Jabeur retired down 0-2 in the second set.
The 2025 season hasn’t been smooth for Jabeur, with health issues and injuries continuing to trouble her. She has now made an early exit in the first round of this year’s grass court Slam, a tournament she dominated in 2022 and 2023, reaching the final both times.
#4 Stefanos Tsitsipas
Another heartbreaking moment unfolded as Stefanos Tsitsipas was forced to withdraw from the tournament due to injury. The 24th seed had to retire from his first-round match against French qualifier Valentine Royer with a back injury, after going down 3-6, 2-6.
Tsitsipas had his best run at the grass-court major in 2023, reaching the Round of 16 before exiting the tournament after a five-set battle against American Christopher Eubanks. He had previously reached the same stage in 2018, when he was defeated by former World No. 8 John Isner. In the second round, Royer will face fellow Frenchman Adrian Mannarino.
#3 Alexei Popyrin
20th seed Alexei Popyrin suffered a first-round exit at the season’s third Grand Slam. The Australian went up against the UK’s Arthur Fery at the All England Club and was defeated in a four-set battle. Popyrin managed to take only the third set, eventually falling 4-6, 1-6, 6-4, 4-6.
The 25-year-old had his best run at Wimbledon in 2024, reaching the round of 32, where he faced Novak Djokovic and lost in four sets. Fery will now take on Italian Luciano Darderi in the second round.
#2 Holger Rune
Another top-seeded player who made a shocking early exit from the Grass Court Slam was Holger Rune. In a surprising first-round upset, the 8th seed in the men’s singles event, Rune, was knocked out by Nicolás Jarry. The Danish star fell to the Chilean despite winning the first two sets. The final score for the Dane was 6-4, 6-4, 5-7, 3-6, 4-6.
Comeback complete 🔁
Nicolas Jarry defeats No.8 seed Holger Rune 4-6, 4-6, 7-5, 6-3, 6-4 🇨🇱#Wimbledon pic.twitter.com/ytsIeeJAUy
— Wimbledon (@Wimbledon) June 30, 2025
Rune’s best run at Wimbledon came in 2023, when he reached the quarterfinals to face two-time defending champion Carlos Alcaraz. However, he was defeated in straight sets. Jarry will now face American Learner Tien in the second round.
#1 Paula Badosa
In possibly the most shocking first-round upset, 9th seed Paula Badosa was knocked out by home-favorite Katie Boulter. The Spaniard fell to the Brit in a hard-fought three-set battle, 2-6, 6-3, 4-6. The 27-year-old’s best run at the grass-court Slam has come when she reached the Round of 16 three times, in 2021, 2022, and 2024, where she fell to Karolína Muchová, Simona Halep, and Donna Vekić, respectively.
Boulter will take on Argentina’s Solana Sierra in her second-round match. While there were several upsets, many top-seeded players on both sides, Carlos Alcaraz, Frances Tiafoe, Jiri Lehecka, Felix Auger-Aliassime, Aryna Sabalenka, and Madison Keys, are still in the event and have advanced to the second round.
