Beaten in five sets after leading 2-0 in the Australian Open final, fifth seed Daniil Medvedev stunned World No.1 Jannik Sinner in a five-set thriller in the men’s singles quarterfinal at Wimbledon on Tuesday. Medvedev also exacted revenge for his other defeat to Sinner at the Miami Open as he earned an epic 6-7(7), 6-4, 7-6(4), 2-6, 6-3 win to snap a five-match losing streak against the Italian.

The match looking taking the usual course as Sinner won a tight first set, but Medvedev had other ideas he came back strongly to alter the course of history. The fifth seed stood deep behind the baseline and went into lockdown mode to grind down the World No. 1, who received a medical timeout in the third set due to illness.

At 1-2, the Italian had his pulse checked by a doctor before he walked off the court to receive further treatment. Sinner continued but had his head in his towel at times during changeovers.

Medvedev ruthlessly took advantage of Sinner’s slight drop in intensity, hitting 55 winners to inflict just a fourth defeat of the season on the World No. 1. With his thrilling four-hour win, Medvedev improved to 7-5 in the pair’s ATP head-to-head series. Tuesday’s quarterfinal marked his first victory against Sinner since the 2023 Miami final.

“I knew if I was going to beat Jannik it was going to be a tough match,” Medvedev was quoted as saying by the ATP Tour in a report on its website. “He is not a guy you are going to beat easily. At one moment he wasn’t feeling too good but he started playing better and I am happy I managed to stay at a high level. There were some great points, it was a great match and I am happy to win and I am looking forward.”

Into his ninth major semifinal (second consecutive at Wimbledon), the No. 5 player in ATP Rankings is chasing his first Grand Slam title since the 2021 US Open. Medvedev will face third-seeded Spaniard Carlos Alcaraz or 12th-seeded American Tommy Paul on Friday.

Sinner has earned a Tour-leading 42 wins this season and was aiming to become the first Italian man to reach multiple Wimbledon semifinals. Sinner lost in the last four to Novak Djokovic last year and was unable to match Medvedev’s consistency and ball-striking in the fifth set in London, where Medvedev was too strong in the gruelling baseline battles.

Under the roof on Centre Court, there was little to separate both in the first set, with a tie-break left to decide the opener. In a low-quality breaker, Medvedev made a string of errors to give Sinner the advantage. The fifth seed double-faulted at 3/1 and missed a backhand return on a Sinner second serve at 4/5. He then fired wide off rally-ball forehands at 6/5 and 6/6, before striking his second double fault of the tie-break at set point down.

Medvedev responded at the start of the second set by breaking in the third game and was the more consistent in the set, committing just six unforced errors compared to 14 from Sinner, who struggled to time the ball. Medvedev did not face a break point in the set, levelling with an ace.

Sinner then received a medical timeout at 1-2 in the third set, with a doctor checking his pulse. Seemingly unwell, the Italian briefly left the court before returning. The top seed did not look overly impaired by the issue but could not regain his lead, with Medvedev finding consistency in the tie-break to lead.

The Italian was dominant on serve in the fourth set, winning 85 percent of points on his first delivery and all five on his second. He also converted his chances on return, winning both break points he earned to force the 36th five-set match of this year’s Championships, an Open Era record at majors.

Medvedev would not be denied in the decider, though. The former ATP Finals champion played front-foot tennis to dictate proceedings, while he refused to miss in the gruelling baseline exchanges to earn his first Top 5 win of the season. Medvedev struck 55 winners to 49 unforced errors, with Sinner holding a 61-45 count.