01/By surface
each with its own count, at equal weight
Hard
4-8
D. leads 8-4 in 12 meetings on hard
Clay
1-2
D. leads 2-1 in 3 meetings on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
15 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Feb 18, 2026 | Qatar Exxon Mobil OpenATP500 | hard | 2nd round | Tsitsipas S. | 6-3, 6-4 | 33 v 11 |
| Oct 9, 2024 | Shanghai MastersMasters 1000 | hard | 4th round | Medvedev D. | 7-6, 6-3 | 12 v 5 |
| Oct 28, 2023 | Vienna OpenATP500 | hard | semifinal | Medvedev D. | 6-4, 7-6 | 7 v 3 |
| May 20, 2023 | Internazionali BNL d'ItaliaMasters 1000 | clay | semifinal | Medvedev D. | 7-5, 7-5 | 5 v 3 |
| Nov 16, 2022 | Masters CupMasters Cup | hard | round robin | Tsitsipas S. | 6-3, 6-7, 7-6 | 3 v 5 |
| Aug 21, 2022 | Western & Southern Financial Group MastersMasters 1000 | hard | semifinal | Tsitsipas S. | 7-6, 3-6, 6-3 | 7 v 1 |
| Jan 28, 2022 | Australian OpenGrand Slam, best of 5 | hard | semifinal | Medvedev D. | 7-6, 4-6, 6-4, 6-1 | 4 v 2 |
| Jun 8, 2021 | French OpenGrand Slam, best of 5 | clay | quarterfinal | Tsitsipas S. | 6-3, 7-6, 7-5 | 5 v 2 |
| Feb 19, 2021 | Australian OpenGrand Slam, best of 5 | hard | semifinal | Medvedev D. | 6-4, 6-2, 7-5 | 6 v 4 |
| Nov 11, 2019 | Masters CupMasters Cup | hard | round robin | Tsitsipas S. | 7-6, 6-4 | 6 v 4 |
| Oct 12, 2019 | Shanghai MastersMasters 1000 | hard | semifinal | Medvedev D. | 7-6, 7-5 | 7 v 4 |
| Apr 18, 2019 | Monte Carlo MastersMasters 1000 | clay | 3rd round | Medvedev D. | 6-2, 1-6, 6-4 | 8 v 14 |
| Oct 26, 2018 | Swiss IndoorsATP500 | hard | quarterfinal | Medvedev D. | 6-4, 3-6, 6-3 | 16 v 20 |
| Aug 29, 2018 | US OpenGrand Slam, best of 5 | hard | 2nd round | Medvedev D. | 6-4, 6-3, 4-6, 6-3 | 15 v 36 |
| Mar 22, 2018 | Sony Ericsson OpenMasters 1000 | hard | 1st round | Medvedev D. | 2-6, 6-4, 6-2 | 70 v 52 |
A record, never a share of meetings. Main-draw singles since 2013; a meeting ended by retirement is counted with the sets that were played and marked; a walkover is listed and counted in neither column. Tsitsipas S. and Medvedev D. each carry the table against every opponent faced.