The Canadian has been a major threat since his tour debut over a decade ago.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
ABN AMRO World Tennis Tournament
|
Quarter Finals | Milos Raonic |
6-2
3-6 4-6 |
| 2012 |
R. M. Keegan Championships
|
1/8 | Milos Raonic |
4-6
4-6 |
| 2010 |
Malaysian Open
Malaysia, Kuala Lumpur |
Championship | Milos Raonic |
7-6
6-7 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Prague
|
1/8 | Sumit Nagal |
6-4
1-6 4-6 |
| 2021 |
Prague
|
1/16 | Sergiy Stakhovsky |
3-6
4-6 |
| 2021 |
Ostrava
|
1/8 | Elias Ymer |
6-1
6-2 |
| 2021 |
Rome
|
1/8 | Lorenzo Giustino |
6-4
6-4 |
| 2021 |
Rome
|
1/16 | Sergiy Stakhovsky |
6-4
3-6 7-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Miami Open
|
1/8 | Hubert Hurkacz |
4-6
6-3 7-6 |
| 2021 |
Miami Open
|
1/16 | Milos Raonic |
4-6
5-7 |
| 2021 |
Miami Open
|
1/32 | Milos Raonic |
2-6
1-6 |
| 2021 |
Mexican Open
|
1/8 | Dominik Koepfer |
6-4
6-2 |
| 2021 |
Mexican Open
|
1/16 | Milos Raonic |
6-7
4-6 |
| 2021 |
Australian Open ATP
|
1/8 | Novak Djokovic |
7-6
4-6 6-1 6-4 |
| 2021 |
Australian Open ATP
|
1/16 | Milos Raonic |
6-7
7-5 2-6 2-6 |
| 2021 |
Australian Open ATP
|
1/32 | Milos Raonic |
7-6
1-6 1-6 4-6 |
| 2021 |
Australian Open ATP
|
1/64 | Milos Raonic |
3-6
3-6 2-6 |
