01/By surface
each with its own count, at equal weight
Hard
6-9
J. leads 9-6 in 15 meetings on hard
Clay
0-1
J. leads 1-0 in 1 meeting on clay
Grass
1-0
D. leads 1-0 in 1 meeting on grass
02/Every meeting
17 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| May 16, 2026 | Internazionali BNL d'ItaliaMasters 1000 | clay | semifinal | Sinner J. | 6-2, 5-7, 6-4 | 9 v 1 |
| Mar 15, 2026 | BNP Paribas OpenMasters 1000 | hard | final | Sinner J. | 7-6, 7-6 | 11 v 2 |
| Nov 14, 2024 | Masters CupMasters Cup | hard | round robin | Sinner J. | 6-3, 6-4 | 4 v 1 |
| Oct 10, 2024 | Shanghai MastersMasters 1000 | hard | quarterfinal | Sinner J. | 6-1, 6-4 | 5 v 1 |
| Sep 5, 2024 | US OpenGrand Slam, best of 5 | hard | quarterfinal | Sinner J. | 6-2, 1-6, 6-1, 6-4 | 5 v 1 |
| Jul 9, 2024 | WimbledonGrand Slam, best of 5 | grass | quarterfinal | Medvedev D. | 6-7, 6-4, 7-6, 2-6, 6-3 | 5 v 1 |
| Mar 29, 2024 | Miami OpenMasters 1000 | hard | semifinal | Sinner J. | 6-1, 6-2 | 4 v 3 |
| Jan 28, 2024 | Australian OpenGrand Slam, best of 5 | hard | final | Sinner J. | 3-6, 3-6, 6-4, 6-4, 6-3 | 3 v 4 |
| Nov 18, 2023 | Masters CupMasters Cup | hard | semifinal | Sinner J. | 6-3, 6-7, 6-1 | 3 v 4 |
| Oct 29, 2023 | Vienna OpenATP500 | hard | final | Sinner J. | 7-6, 4-6, 6-3 | 3 v 4 |
| Oct 4, 2023 | China OpenATP500 | hard | final | Sinner J. | 7-6, 7-6 | 3 v 7 |
| Apr 2, 2023 | Miami OpenMasters 1000 | hard | final | Medvedev D. | 7-5, 6-3 | 5 v 11 |
| Feb 19, 2023 | ABN AMRO World Tennis TournamentATP500 | hard | final | Medvedev D. | 5-7, 6-2, 6-2 | 11 v 14 |
| Oct 28, 2022 | Vienna OpenATP500 | hard | quarterfinal | Medvedev D. | 6-4, 6-2 | 4 v 12 |
| Nov 18, 2021 | Masters CupMasters Cup | hard | round robin | Medvedev D. | 6-0, 6-7, 7-6 | 2 v 11 |
| Mar 12, 2021 | Open 13ATP250 | hard | quarterfinal | Medvedev D. | 6-2, 6-4 | 3 v 34 |
| Feb 20, 2020 | Open 13ATP250 | hard | 2nd round | Medvedev D. | 1-6, 6-1, 6-2 | 5 v 68 |
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. Medvedev D. and Sinner J. each carry the table against every opponent faced.