| No. of times Played | 8 |
|
|
|
| Win % | 75% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | Roland Garros | Tournament | ATP Masters 1000 Canada |
| Round | Finals | Round | Round of 16 |
| Winner | Novak Djokovic | Winner | Stefanos Tsitsipas |
| Score | 76 | Score | 63 67 |
| No. of times Played | 8 |
|
|
|
| Win % | 75% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | Roland Garros | Tournament | Basel |
| Round | Quarter-Finals | Round | Quarter-Finals |
| Winner | Stefanos Tsitsipas | Winner | Daniil Medvedev |
| Score | 63 76 | Score | 46 63 36 |
| No. of times Played | 9 |
|
|
|
| Win % | 33% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | ATP Masters 1000 Cincinnati | Tournament | ATP Masters 1000 Canada |
| Round | Semi-Finals | Round | Quarter-Finals |
| Winner | Alexander Zverev | Winner | Stefanos Tsitsipas |
| Score | 46 63 67 | Score | 36 76 |
| No. of times Played | 9 |
|
|
|
| Win % | 78% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | Barcelona | Tournament | ATP Masters 1000 Canada |
| Round | Finals | Round | Finals |
| Winner | Rafael Nadal | Winner | Rafael Nadal |
| Score | 46 76 | Score | 26 67 |
| No. of times Played | 8 |
|
|
|
| Win % | 50% |
| H2H |
| Last Played | 2021 | First Played | 2017 |
| Tournament | ATP Masters 1000 Monte Carlo | Tournament | Quimper |
| Round | Finals | Round | Round of 32 |
| Winner | Stefanos Tsitsipas | Winner | Andrey Rublev |
| Score | 63 63 | Score | 26 63 67 |
| No. of times Played | 8 |
|
|
|
| Win % | 25% |
| H2H |
| Last Played | 2021 | First Played | 2018 |
| Tournament | ATP Masters 1000 Miami | Tournament | Next Gen ATP Finals |
| Round | Quarter-Finals | Round | Round Robin |
| Winner | Hubert Hurkacz | Winner | Stefanos Tsitsipas |
| Score | 62 36 46 | Score | 41 43 |
| No. of times Played | 6 |
|
|
|
| Win % | 33% |
| H2H |
| Last Played | 2021 | First Played | 2017 |
| Tournament | Roland Garros | Tournament | ATP Masters 1000 Shanghai |
| Round | Round of 32 | Round | Round of 32 |
| Winner | Stefanos Tsitsipas | Winner | John Isner |
| Score | 57 63 76 | Score | 67 |
| No. of times Played | 8 |
|
|
|
| Win % | 63% |
| H2H |
| Last Played | 2020 | First Played | 2018 |
| Tournament | Nitto ATP Finals | Tournament | ATP Masters 1000 Canada |
| Round | Round Robin | Round | Round of 32 |
| Winner | Dominic Thiem | Winner | Stefanos Tsitsipas |
| Score | 67 | Score | 63 76 |
