01/By surface
each with its own count, at equal weight
Hard
0-3
D. leads 3-0 in 3 meetings on hard
Clay
Never on clay
no meeting on this surface
Grass
Never on grass
no meeting on this surface
02/Every meeting
3 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, M. first |
|---|---|---|---|---|---|---|
| Nov 7, 2020 | BNP Paribas MastersMasters 1000 | hard | semifinal | Medvedev D. | 6-4, 7-6 | 17 v 5 |
| Jan 4, 2019 | Brisbane InternationalATP250 | hard | quarterfinal | Medvedev D. | 6-7, 6-3, 6-4 | 18 v 16 |
| Oct 5, 2018 | Rakuten Japan Open Tennis ChampionshipsATP500 | hard | quarterfinal | Medvedev D. | 7-6, 6-3 | 20 v 32 |
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. Raonic M. and Medvedev D. each carry the table against every opponent faced.