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