Hurkacz escaped, ten others didn’t: The men still winless in 8+ matches against Djokovic

For eight meetings, Hubert Hurkacz belonged to one of the least enviable lists in tennis: the men who played Novak Djokovic again and again and never won. On Friday in Shanghai he left it, beating a visibly tired Djokovic 6-4, 6-3 in the second round, just days after the Serb had won the Beijing title. It was the Pole's ninth attempt, and it is a reminder of how hard that exit is to find.

Because the point of this list is not simply that these players lost to Djokovic. Hundreds of men have done that. The point is how many chances they got. Ten players have faced him at least eight times without winning once, and together they account for 109 matches and zero victories. Monfils alone has lost 20 times, Chardy 14, Raonic and Seppi 12 each, Fritz 11, and five more players sit on eight.

What is striking is who they are. This is not a group of journeymen who drew him in the first round and moved on. It includes former top-10 players, Grand Slam semifinalists and a Wimbledon finalist, men who reached the second week of majors precisely because they were good enough to meet him there. Here is who they are, what they came closest to doing, and why the numbers look the way they do.

The picture that emerges is of an era more than a group of rivals. Monfils, Chardy, Raonic and Seppi are separated from Djokovic by more than a decade of results, and their records span the whole arc of his career, from the 2005 US Open to this year. In other words, this isn't a list of players who happened to catch him on bad days. It is a list of players who kept getting a chance.

No one has lost more often to Djokovic without winning than Monfils, and their record is the most one-sided in the Open Era, ahead of Nadal's 18-0 over Richard Gasquet. The rivalry began at the 2005 US Open, when an 18-year-old Djokovic needed five sets to beat him, 7-5, 4-6, 7-6(5), 0-6, 7-5. Monfils won a set 6-0 in that match, which tells you how close the start of this story was. They have played 20 times since, across Slams (5-0 for Djokovic), Masters 1000 events (9-0), the Olympics, Davis Cup and ATP Cup.

The closest he came was the 2009 Paris Masters final, when Monfils held a break in the deciding set before losing 6-2, 5-7, 7-6(3). Over the following years it became a dynamic more than a rivalry: Monfils's athletic, improvisational tennis produced spectacular points but rarely survived Djokovic's returning.

By 2023 in Cincinnati, Monfils was asking for Djokovic's shirt after a 6-3, 6-2 defeat, and Djokovic signed it with the words "sorry not sorry." The latest meeting, a 6-3, 6-3 win in Brisbane in January 2025, took 1 hour and 12 minutes, and Djokovic converted all three break points he created.

Chardy's case is the most extreme in terms of sets: he has reportedly never taken one from Djokovic in 14 meetings. When they met at Wimbledon in 2011, Chardy had gone five matches without winning a set against him, and he lost that one 6-4, 6-1, 6-1 in 1 hour and 20 minutes. The first meeting came in the 2009 Australian Open, a 7-5, 6-1, 6-3 win, and the last in the first round of the 2021 Australian Open, 6-3, 6-1, 6-2.

The split by surface shows how complete it was: 7-0 on hard courts, 3-0 on clay, 3-0 on grass and 1-0 indoors. A match in Madrid in 2019 was the nearest thing to resistance, a 6-1, 7-6 win in the third round. It is a particularly harsh record for a player who built a long career on a heavy forehand and a first serve that troubled many top-20 opponents, and it shows that he simply never found the pattern that would let him win a set against this particular opponent.

Raonic is the most interesting case on the list, because he was the one whose game should have worried Djokovic. A big server and a Wimbledon finalist in 2016, he first faced Djokovic in the 2013 Davis Cup, losing 7-6(1), 6-2, 6-2. By 2021 they had met 12 times, and Raonic had won just four sets, while Djokovic had won eight of the first nine tie-breaks they played.

The closest he came was in the 2020 Cincinnati final, when he won the first set 6-1 and then lost 1-6, 6-3, 6-4. The last meeting came in the fourth round of the 2021 Australian Open, a 7-6(4), 4-6, 6-1, 6-4 win for Djokovic in which Raonic hit 26 aces. They had also met in the 2018 French Open quarterfinals. The record reflects a simple fact: a good serve can win you a set against Djokovic, but it takes a lot more to win a match.

Seppi's record reads strangely against his reputation. He is a player capable of beating some of the best in the game, and Djokovic still beat him 12 times in a row between 2006 and 2016. The first meeting was in Rotterdam in 2006, a 6-2, 2-6, 7-5 win for the Serb. Seppi would win only four sets in total over the whole series.

Two Grand Slam meetings stand out. At the 2015 US Open, in the third round, Djokovic won 6-3, 7-5, 7-5. At the 2016 Australian Open, the last meeting, he won 6-1, 7-5, 7-6(6) after being pushed to a tie-break in the third set. It was the kind of match that shows why the record exists: Seppi was competitive in the final two sets of that match, and still lost both.

Fritz is the youngest man on the list and the only one who is an active top-10 player, which makes him the most likely to follow Hurkacz out. Their first meeting was a 6-3, 6-0 win for Djokovic in Monte Carlo in 2019. Since then they have met repeatedly at the majors: the 2021 Australian Open third round (7-6(1), 6-4, 3-6, 4-6, 6-2, a match in which Fritz took his first sets), the 2023 US Open quarterfinal (6-1, 6-4, 6-4), the 2024 Australian Open quarterfinal (7-6(3), 4-6, 6-2, 6-3) and the 2025 US Open quarterfinal.

He also lost the 2024 Shanghai semifinal 6-4, 7-6(6), and he had won only three sets in the first ten meetings, so it is a record built on narrow margins rather than blowouts. Hurkacz's win was built on his serve: 13 aces, 82% of first-serve points won and only two break points faced. Fritz has the same weapon, and if Djokovic keeps showing fatigue at the end of long weeks, he is the obvious next name to come off the list.

Jan-Lennard Struff's most recent defeat came in the fourth round of the 2025 US Open, where he lost 6-3, 6-3, 6-2 in one hour and 49 minutes. Struff had come through qualifying and beaten Holger Rune and Frances Tiafoe to reach that stage. Earlier meetings included a 6-2, 6-4 victory for Djokovic at the 2021 Davis Cup Finals. Their eight matches have taken place across six hard-court encounters, one indoors and one on clay. Despite his powerful serve, Struff has never managed to win a set against Djokovic at Grand Slam level.

Denis Shapovalov came closest to a breakthrough at Wimbledon in 2021, when he lost their semifinal 7-6, 7-5, 7-5, with each set decided by a tiebreak or a single break of serve. They also met at the 2021 ATP Cup, where Djokovic won 7-5, 7-5, and in the Adelaide quarterfinals in 2023, where the Serbian prevailed 6-3, 6-4. Across their eight meetings, Shapovalov has managed to win just two sets.

Fabio Fognini, a former top-10 player and Masters 1000 finalist, never found a way past Djokovic despite his considerable talent. He suffered a 6-3, 6-0, 6-2 defeat in the fourth round of the 2014 Australian Open, while their most recent meeting ended in a 6-3, 6-3 loss for the Italian in the second round of the 2016 Shanghai Masters. Their head-to-head record reflects Djokovic's consistent ability to neutralise Fognini's game.

Marcos Baghdatis is perhaps the most memorable case. The Cypriot faced Djokovic in the 2007 Wimbledon quarterfinals on Court One in a five-set battle lasting around five hours. Djokovic eventually prevailed 7-6, 7-6, 6-7, 4-6, 7-5, breaking serve at 5-5 in the deciding set before serving out the match. The physical toll was considerable: Djokovic subsequently retired during his semifinal against Rafael Nadal.

Juan Monaco belongs to an earlier generation of Argentine clay-court specialists. Djokovic took control of their rivalry from their first meeting at Wimbledon in 2005, the year the tournament introduced its now-familiar player interview booths at SW19. That encounter marked an early step in Djokovic's development on London's grass courts. Monaco managed to win only two sets across their eight meetings, which included a fourth-round clash at the 2007 US Open and a semifinal at the 2012 Miami Open.