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Daniil Medvedev beats Novak Djokovic to reach the semi-finals of an ATP Masters 1000 event for the first time.

Medvedev Upsets Djokovic In Monte-Carlo

Russian to face Lajovic for spot in Masters 1000 final

Daniil Medvedev entered the Rolex Monte-Carlo Masters with two victories from 11 tour-level matches on clay, but that didn't stop the Russian from claiming the biggest victory of his career on Friday.

The 23-year-old stunned Novak Djokovic 6-3, 4-6, 6-2, breaking the two-time former champion on five occasions to reach his first ATP Masters 1000 semi-final. Medvedev had lost each of his previous three FedEx ATP Head2Head encounters against Djokovic, but claimed his first victory over a World No. 1 after two hours and 20 minutes to move into the last four.

"It's definitely the best match of my career. Not in terms of level of tennis, but definitely by the result. [It's my] first Masters 1000 semi-final, beating No. 1 for the first time in my life," Medvedev said. "[It's] just amazing."

Two days ago, Medvedev owned a 1-11 record against opponents inside the Top 10 of the ATP Rankings. With back-to-back victories over World No. 8 Stefanos Tsitsipas and top-ranked Djokovic, the Sofia Open winner is two wins away from his maiden Masters 1000 crown.

Medvedev is just the second man to defeat Djokovic in nine quarter-finals at the Monte-Carlo Country Club. Belgian David Goffin became the first man to achieve the feat in 2017.

"He's got a very solid backhand. He doesn't make many mistakes from the backhand. He hits it very low with depth. A windy day like today, conditions are changing every single game. It's kind of tough to find the rhythm, and he doesn't give you much rhythm," Djokovic said. "He improved his movement a lot since last year. He definitely deserves to be where he is."

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Standing between Medvedev and a place in the final will be another Serbian oppponent; Dusan Lajovic. The World No. 48 backed up his shock win over World No. 5 Dominic Thiem with a 6-4, 7-5 victory against Italian qualifier Lorenzo Sonego.

Alongside his title run in Sofia, Medvedev also advanced to the championship match at the Brisbane International (l. to Nishikori). The four-time ATP Tour titlist owns a tour-leading 21 victories this season (21-6), which is three more than second-placed Roger Federer (18-2) and Stefanos Tsitsipas (18-8). Medvedev was one of just two players (also Shapovalov) to take a set from Djokovic at this year's Australian Open.

"He played worse than he did the times before and also I'm getting more experienced. I'm starting to make these top guys know that it's tough to play against me," Medvedev said. "In Australia he was at his best, but I made him run for the win and I was happy about my game. Here I knew if I kept up the level I had in Australia I would have my chances."

Under heavy winds on Court Rainier III, Medvedev made the perfect start with a service break in the opening game. The Russian proved impenetrable from the baseline, with Djokovic failing to find the court after pressing with his forehand in extended rallies. Medvedev maintained his level from the back of the court, keeping his error count low to break for a second time and take the opening set. Djokovic committed 21 unforced errors compared to Medvedev's six in the 39-minute opener.

Read: Why Djokovic's No. 1 Ranking Is Safe... For Now

But Djokovic found his rhythm, grabbing a 2-1 lead in the second set with impeccable touch. The World No. 1 brought Medvedev into the net behind a well-placed backhand drop shot, before grabbing the break with a backhand lob. Djokovic held his advantage through to 5-4, where he levelled the match with back-to-back aces.

Medvedev was not deterred, though, capitalising on three consecutive unforced errors from Djokovic to take a 3-1 lead in the decider. Two games later, the tenth seed outmanoeuvred Djokovic in net exchanges to grab a second break. Despite failing to serve out the match on his first opportunity, Medvedev broke Djokovic for the fifth time with a backhand winner to claim victory.

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Djokovic was bidding to reach his first tour-level semi-final since capturing a record-breaking seventh title at the Australian Open in January (d. Nadal). The World No. 1, who has lifted two titles in Monte-Carlo (2013, '15), drops to 34-11 at the opening Masters 1000 event of the European clay swing.