Three upsets on Day 1 of 2025 Wimbledon

Carlos Alcaraz was pushed to five sets only twice en route to back-to-back Wimbledon titles in 2023 and 2024. In a stunning turn of events, the Spaniard endured a five-setter on Monday, nearly suffering what would have been the biggest first-round upset in Wimbledon history. 

While Alcaraz escaped with a win, several other top-ranked players were unable to advance to the second round at SW19.

World No. 8 Holger Rune

The Dane raced to a two-set lead before his right knee started to bother him, opening the door for World No. 143 Nicolas Jarry to script an improbable comeback. Jarry had never won a five-set match during his 11 years on the Tour — until Monday. Furthermore, he walked into the match with a 6-13 record in 2025. After his loss, Rune refused to give his opponent any credit, citing his knee injury for the loss.

World No. 9 Daniil Medvedev

The fall from grace continues. The former World No. 1 and 2021 U.S. Open winner has been in horrendous form lately, losing in the second round at the Australian Open, the first round at Roland-Garros and now the opening round at Wimbledon. The string of results marks his worst showing over three slams since 2017. On Monday, he appeared defeated after losing the first-set tiebreaker, barely putting up a fight the rest of the way in his loss to World No. 42 Benjamin Bonzi. The Russian committed 47 unforced errors and converted only 2-of-8 break points, lacking the killer instinct to put away his lesser opponent.  

World No. 9 Paula Badosa

Unlike Medvedev, the Spaniard started the year with a bang, reaching the semifinals at the Australian Open and making deep runs at Dubai and Miami. However, her road to Wimbledon wasn't ideal. After a disappointing clay-court swing, she was forced to retire from the Berlin Open, her only grass-court warm-up for Wimbledon, with a back injury. Her lack of preparation was evident in Monday's loss to Katie Boulter. Badosa could get only 58 percent of her first serves in (52/89), and the baseliner's refusal to approach the net cost her, too, with Boulter winning 12-of-13 of her net points to breeze to a relatively easy 6-2, 3-6, 6-4 win.

Several other upsets...

Other notable players who were upset on Monday include World No. 14 Andrey Rublev, who lost to Serbian wildcard Laslo Djere; World No. 19 Francisco Cerundolo, who fell to Portuguese World No. 32 Nuno Borges; and World No. 22 Alexei Popyrin, who suffered a shocking loss to World No. 461 Arthur Fery. 

On the women's side, World No. 21 Jeļena Ostapenko lost to British wildcard Sonay Kartal, and Ons Jabeur, a two-time Wimbledon finalist, medically retired against Viktoriya Tomova.

So, who's on upset alert in Day 2? 

World No. 18 Ugo Humbert will have his hands full against 38-year-old journeyman Gael Monfils, a crowd favorite at the All England Tennis Club. On the women's side, World No. 3 Jessica Pegula will be tested by Elisabetta Cocciaretto, an improved player who made deep runs at several WTA-250 grass-court events in the lead up to Wimbledon.