01/By surface
each with its own count, at equal weight
Hard
2-3
D. leads 3-2 in 5 meetings on hard
Clay
Never on clay
no meeting on this surface
Grass
Never on grass
no meeting on this surface
02/Every meeting
5 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| Oct 30, 2022 | Vienna OpenATP500 | hard | final | Medvedev D. | 4-6, 6-3, 6-2 | 19 v 4 |
| Aug 18, 2022 | Western & Southern Financial Group MastersMasters 1000 | hard | 3rd round | Medvedev D. | 7-5, 7-5 | 21 v 1 |
| Oct 6, 2018 | Rakuten Japan Open Tennis ChampionshipsATP500 | hard | semifinal | Medvedev D. | 6-3, 6-3 | 31 v 32 |
| Aug 1, 2018 | Citi OpenATP500 | hard | 2nd round | Shapovalov D. | 3-6, 6-1, 6-4 | 26 v 63 |
| Aug 28, 2017 | US OpenGrand Slam, best of 5 | hard | 1st round | Shapovalov D. | 7-5, 6-1, 6-2 | 69 v 54 |
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. Shapovalov D. and Medvedev D. each carry the table against every opponent faced.