Andrey Rublev and Iga Swiatek would be ranked No. 3, and Naomi Osaka a clear No. 1.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Delray Beach Open
|
1/16 | Milos Raonic |
2-6
2-6 |
| 2017 |
Open Parc Auvergne-Rhone-Alpes Lyon
|
1/8 | Milos Raonic |
6-4
6-3 |
| 2014 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Milos Raonic |
6-7
3-6 |
| 2013 |
SAP Open
United States, California, San Jose |
Quarter Finals | Milos Raonic |
7-6
6-3 |
| 2012 |
SAP Open
United States, California, San Jose |
Final | Milos Raonic |
7-6
6-2 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Nur-Sultan 2
|
1/8 | Taro Daniel |
6-2
6-4 |
| 2021 |
Nur-Sultan
|
1/8 | Mackenzie McDonald |
6-2
6-3 |
