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BUL ATP
5
vs
2
CAN ATP
By surface
| Surface | Grigor Dimitrov | Milos Raonic |
| Hard |
5 |
1 |
| Clay |
0 |
1 |
All meetings (7)
| Date | Tour | Tournament | Round | Surface | Winner |
Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
| 2020-10-19 |
ATP |
Antwerp |
Quarterfinal |
Hard |
Grigor Dimitrov |
W/O |
| 2018-05-07 |
ATP |
Madrid Masters |
Round of 32 |
Clay |
Milos Raonic |
5-7 |
6-3 |
3-6 |
|
|
| 2017-01-02 |
ATP |
Brisbane |
Semifinal |
Hard |
Grigor Dimitrov |
7-67 |
6-2 |
|
|
|
| 2016-10-03 |
ATP |
Beijing |
Semifinal |
Hard |
Grigor Dimitrov |
W/O |
| 2014-01-13 |
ATP |
Australian Open |
Round of 32 |
Hard |
Grigor Dimitrov |
6-3 |
3-6 |
6-4 |
7-610 |
|
| 2012-12-30 |
ATP |
Brisbane |
Round of 16 |
Hard |
Grigor Dimitrov |
6-3 |
6-4 |
|
|
|
| 2011-10-17 |
ATP |
Stockholm |
Quarterfinal |
Hard |
Milos Raonic |
5-7 |
4-6 |
|
|
|