01/By surface
each with its own count, at equal weight
Hard
1-1
Level 1-1 in 2 meetings on hard
Clay
0-1
M. leads 1-0 in 1 meeting on clay
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, O. first |
|---|---|---|---|---|---|---|
| May 3, 2016 | Mutua Madrid OpenMasters 1000 | clay | 2nd round | Raonic M. | 6-4, 6-7, 6-2 | 29 v 10 |
| Mar 17, 2015 | BNP Paribas OpenMasters 1000 | hard | 3rd round | Raonic M. | 7-6, 6-4 | 41 v 6 |
| Mar 13, 2014 | BNP Paribas OpenMasters 1000 | hard | quarterfinal | Dolgopolov O. | 6-3, 6-4 | 31 v 11 |
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. Dolgopolov O. and Raonic M. each carry the table against every opponent faced.