01/By surface
each with its own count, at equal weight
Hard
4-1
D. leads 4-1 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 |
|---|---|---|---|---|---|---|
| Aug 6, 2026 | Canadian OpenMasters 1000 | hard | 2nd round | Van De Zandschulp B. | 6-3, 7-6 | 6 v 70 |
| Feb 16, 2023 | ABN AMRO World Tennis TournamentATP500 | hard | 2nd round | Medvedev D. | 6-2, 6-2 | 11 v 35 |
| Aug 17, 2022 | Western & Southern Financial Group MastersMasters 1000 | hard | 2nd round | Medvedev D. | 6-4, 7-5 | 1 v 24 |
| Jan 22, 2022 | Australian OpenGrand Slam, best of 5 | hard | 3rd round | Medvedev D. | 6-4, 6-4, 6-2 | 2 v 57 |
| Sep 7, 2021 | US OpenGrand Slam, best of 5 | hard | quarterfinal | Medvedev D. | 6-3, 6-0, 4-6, 7-5 | 2 v 117 |
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 Van De Zandschulp B. each carry the table against every opponent faced.