Novak Djokovic saw his bid for a sixth ATP Finals title suffer a setback on Wednesday night after the world No 1 was soundly beaten by Russia's Daniil Medvedev.
Djokovic could have booked his place in the semi-finals following his straight sets win over eighth seed Diego Schwartzman in his opening Group Tokyo 1970 match, but instead it was Medvedev who guaranteed his passage with a 6-3, 6-3 win over the top seed.
Top seed Djokovic is seeking to match the record of six-time winner Roger Federer, who is absent from the season-ending tournament with an injury.
But Medvedev, who won the Paris Masters last week, beat Djokovic at his own game, grinding him down in a near-flawless defensive display.
The Russian earned a clutch of early break points and eventually made one count in the seventh game, which lasted 11 gruelling minutes.
Medvedev, 24, held serve easily in the next game and seized the opening set when a rattled Djokovic double-faulted.
An increasingly confident Medvedev broke the 17-time Grand Slam champion again at the start of the second set to win his sixth game in a row in the round-robin match.
Djokovic stopped the slide on his own serve but was able to force just one break point, which he could not convert.
The victory takes Medvedev through to the semi-finals but five-time winner Djokovic still has a chance to progress in a shootout with Zverev on Friday.
"Always I like to pay Novak, first of all because he's one of the greatest champions in the history of our sport and when I was eight years old I was already watching him on TV winning Grand Slams," said Medvedev.
"He was still young – so it was always a dream come true to play against him."
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ATP Finals: Player profiles
The eight players competing in the 2020 ATP Finals in London. Click or swipe through the gallery to read the player profiles. Getty Images
1. Novak Djokovic (11830 points): Titles in 2020 – 4 / Prize money in 2020 – $5,976,158. Another exemplary year for the world No 1, starting with successive titles Down Under where he led Serbia to the inaugural ATP Cup, before winning a record-extending eighth Australian Open title. The Serb maintained his unbeaten run by clinching the Dubai and Western & Southern Open titles. Djokovic’s perfect season was only halted by his US Open disqualification, but he quickly bounced back by winning the Rome Masters. A five-time winner of the ATP Finals, Djokovic is aiming for a sixth title after confirming his position as year-end No 1 for a sixth time.
2. Rafael Nadal (9850 points): Titles in 2020 – 2 / Prize money in 2020 – $3,397,127. Only played in six tournaments this season, owing mainly to the coronavirus pandemic, but Nadal still managed to lift his third trophy in Acapulco and claimed a 13th French Open title having opted to skip his US Open title defence to prepare. The Spaniard has been a near-permanent fixture in the ATP Finals for a generation, but despite being a two-time finalist, is yet to win the season-ending event. Reuters
3. Dominic Thiem (9125 points): Titles in 2020 – 1 / Prize money in 2020 – $5,163,876. Only one title this season for Thiem but what a big title it was as the Austrian won his maiden Grand Slam at the US Open. Also made the Australian Open final where he went down to Djokovic in five sets. Appearing at the ATP Finals for a fifth straight year, Thiem is aiming to go one better after reaching last year’s final. Getty Images
4. Daniil Medvedev (6970 points): Titles in 2020 – 1 / Prize money in 2020 – $2,043,670. After a superb breakthrough in 2019, Medvedev was not able to hit the same heights this season but enters the ATP Finals having won the Paris Masters last time out. Returning to London for a second straight year, the Russian will hope to improve on his 2019 showing when he lost all three group matches. Getty Images
5. Stefanos Tsitsipas (5925 points): Titles in 2020 – 1 / Prize money in 2020 – $1,787,232. Just the one trophy this year for the Greek, who successfully defended his Marseille Open title while reaching two further finals in Dubai and Hamburg. Tsitsipas claimed the biggest title of his career last year when he won the ATP Finals on debut. Will become the first player since Djokovic in 2015 if he retains the title. Getty Images
6. Alexander Zverev (5525 points): Titles in 2020 – 2 / Prize money in 2020 – $2,949,077. Zverev claimed back-to-back titles in Cologne this season and continued his late season form by reaching the Paris Masters final. Made his big Grand Slam breakthrough by making the US Open final where he led by two sets. Won the ATP Finals in 2018. Getty Images
7. Andrey Rublev (3919 points): Titles in 2020 – 5 / Prize money in 2020 – $1,863,487. The breakthrough year he’s been threatening to have for some time. Now injury-free, Rublev racked up five titles, in Doha, Adelaide, Hamburg, St Petersburg, and Vienna. Making his ATP Finals debut. Getty Images
8. Diego Schwartzman (3455 points): Titles in 2020 – 0 / Prize money in 2020 – $1,397,441. No titles for the Argentine this year but some fine performances, including a run to the Rome Masters final, where he beat Rafael Nadal en route, and further finals in Cologne and Cordoba. Making his ATP Finals debut. Getty Images
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"I was serving good and playing safe enough in the most important moments and that's why I got the win," added the Russian, who lost all three of his matches on his debut last year.
Djokovic has until Friday to regroup and will take on Zverev in what will be a winner-takes-all contest. The 34-year-old Serb has played the German twice at the ATP Finals, with Zverev winning the first encounter in the 2018 final, before Djokovic took his revenge 12 months later in a group stage match.
“He was just better, no question about it,” Djokovic said after his defeat to Medvedev. ”Just not a great match from my side. I thought I could have and should have done better, but credit to him for playing on a high level.”
Djokovic's long-time rival Rafael Nadal also has it all to play for in his final Group London 2020 match when the Spanish second seed takes on Stefanos Tsitsipas on Thursday evening.
Nadal, 34, has lost to Tsitsipas, seeded fifth this week, just once in six meetings — at the 2019 Madrid Open. He beat Tsitsipas here last year in the round robin before the 22-year-old Greek went on to win the title.
Nadal has never won the ATP Finals.
Also Thursday, Dominic Thiem, who has already qualified for the semifinals, faces Andrey Rublev. The Russian is 0-2 and can't advance.