Novak Djokovic and Denis Shapovalov have crossed paths a number of times since their first meeting in 2019.
Shapovalov was a promising teenager at the time, having previously reached the fourth round of the US Open as an 18-year-old.
Coming into the 2019 Australian Open as the 25th seed, Shapovalov beat Pablo Andujar and Taro Daniel to reach the third round in Melbourne for the first time.
This set up a first-time meeting with Djokovic, who was a six-time Australian Open champion at the time.
What Novak Djokovic said he liked about Denis Shapovalov at the 2019 Australian Open
Despite taking a set off the top seed, Shapovalov saw his run come to an end at the hands of Djokovic, who went onto win his seventh Australian Open title that year.
In his post-match press conference after the match, Djokovic was asked about what the difference was between seeing Shapovalov compete and playing against him.
When answering this question, Djokovic explained that he was particularly impressed with Shapovalov’s mentality.
“Well, he’s got pretty complete game,” said Djokovic. “He’s got the big serve, a lot of rotation on the ball. He can hit it flat. He can hit it with a spin. I like his mentality. I like his confidence in himself, his approach. He’s very positive on the court, always backing himself up. I like that.
“Obviously he’s lacking some experience playing on the big stage in the big matches, but that’s going to come. I like the way he plays. He seems like a guy who dedicates a lot of time to training and to the process of understanding of how he can improve. These kind of experiences can only help him.”
Since that match, Shapovalov and Djokovic have played each other seven more times, including in the Paris Masters final later that year and their perhaps most significant meeting came in the 2021 Wimbledon semi-final.
In their eight matches against one another, Djokovic has beaten Shapovalov every time and six of these matches have been straight sets victories for the Serbian.
These meetings have contributed to Shapovalov calling Djokovic the ‘GOAT’ over Roger Federer and Rafael Nadal.
| Year | Tournament | Result |
| 2019 | Australian Open R32 | Djokovic beat Shapovalov, 6-3 6-4 4-6 6-0 |
| 2019 | Italian Open R32 | Djokovic beat Shapovalov, 6-1 6-3 |
| 2019 | Shanghai Masters R32 | Djokovic beat Shapovalov, 6-3 6-3 |
| 2019 | Paris Masters Final | Djokovic beat Shapovalov, 6-3 6-4 |
| 2020 | ATP Cup QF | Djokovic beat Shapovalov, 4-6 6-1 7-6(4) |
| 2021 | ATP Cup Round-robin | Djokovic beat Shapovalov, 7-5 7-5 |
| 2021 | Wimbledon SF | Djokovic beat Shapovalov, 7-6(3) 7-5 7-5 |
| 2023 | Adelaide International QF | Djokovic beat Shapovalov, 6-3 6-4 |
Novak Djokovic congratulates Denis Shapovalov on his Dallas Open victory
Although he has never been able to beat Djokovic, Shapovalov made history at the Dallas Open after winning his third title.
The 25-year-old had to come through many top ranked opponents to win the ATP 500 tournament, with victories over Taylor Fritz, Tommy Paul and Casper Ruud in the final.
This has enabled Shapovalov to climb 22 places in the latest ATP rankings update back up to world number 32.
Following the biggest singles title win of Shapovalov’s career, Djokovic reached out in a message on Instagram.
In a reply on Shapovalov’s Instagram post, Djokovic said, “Bravo (clapping emoji). Shapoooo (trophy and strong arm emoji).
Djokovic is one of a number of people to congratulate the Dallas Open champion, with Auger-Aliassime also congratulating Shapovalov on his win.
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