01/By surface
each with its own count, at equal weight
Hard
2-2
Level 2-2 in 4 meetings on hard
Clay
1-0
D. leads 1-0 in 1 meeting on clay
Grass
1-0
D. leads 1-0 in 1 meeting on grass
02/Every meeting
6 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| Aug 1, 2025 | Canadian OpenMasters 1000 | hard | 3rd round | Popyrin A. | 5-7, 6-4, 6-4 | 14 v 26 |
| May 11, 2025 | Internazionali BNL d'ItaliaMasters 1000 | clay | 3rd round | Medvedev D. | 6-4, 6-1 | 11 v 25 |
| Oct 30, 2024 | BNP Paribas MastersMasters 1000 | hard | 2nd round | Popyrin A. | 6-4, 2-6, 7-6 | 5 v 24 |
| Mar 28, 2021 | Miami OpenMasters 1000 | hard | 3rd round | Medvedev D. | 7-6, 6-7, 6-4 | 2 v 86 |
| Jan 25, 2020 | Australian OpenGrand Slam, best of 5 | hard | 3rd round | Medvedev D. | 6-4, 6-3, 6-2 | 4 v 96 |
| Jul 3, 2019 | WimbledonGrand Slam, best of 5 | grass | 2nd round | Medvedev D. | 6-7, 6-1, 6-4, 6-4 | 13 v 101 |
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 Popyrin A. each carry the table against every opponent faced.