4-1
G. leads 4-1, 5 meetings, 2013 to 2020, 1 walkover not counted
01/By surface
each with its own count, at equal weight
Hard
4-0
G. leads 4-0 in 4 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
6 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, G. first |
|---|---|---|---|---|---|---|
| Oct 23, 2020 | European OpenATP250 | hard | quarterfinal | Dimitrov G.ret. | no set played | 20 v 19 |
| May 8, 2018 | Mutua Madrid OpenMasters 1000 | clay | 2nd round | Raonic M. | 7-5, 3-6, 6-3 | 4 v 24 |
| Jan 7, 2017 | Brisbane InternationalATP250 | hard | semifinal | Dimitrov G. | 7-6, 6-2 | 17 v 3 |
| Oct 8, 2016 | China OpenATP500 | hard | semifinal | Dimitrov G.walkover, not counted | no set played | 20 v 6 |
| Jan 18, 2014 | Australian OpenGrand Slam, best of 5 | hard | 3rd round | Dimitrov G. | 6-3, 3-6, 6-4, 7-6 | 22 v 11 |
| Jan 3, 2013 | Brisbane InternationalATP250 | hard | 2nd round | Dimitrov G. | 6-3, 6-4 | 48 v 13 |
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. Dimitrov G. and Raonic M. each carry the table against every opponent faced.