| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Citi Open
|
1/8 | Kei Nishikori |
6-7
3-6 |
| 2018 |
Abierto Mexicano Telcel
|
1/16 | Denis Shapovalov |
7-6
3-6 1-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
US Open ATP
|
1/16 | Alex De Minaur |
6-2
6-4 2-6 6-3 |
| 2019 |
US Open ATP
|
1/32 | Kei Nishikori |
2-6
6-4 3-6 5-7 |
| 2019 |
US Open ATP
|
1/64 | Kei Nishikori |
1-6
1-4 |
| 2019 |
Western & Southern Open
|
1/16 | Yoshihito Nishioka |
6-7
4-6 |
| 2019 |
Rogers Cup
|
1/16 | Richard Gasquet |
6-7
6-2 7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Intrum Stockholm Open
|
Final | Denis Shapovalov |
6-4
6-4 |
| 2019 |
Intrum Stockholm Open
|
Semi Finals | Denis Shapovalov |
5-7
2-6 |
| 2019 |
Intrum Stockholm Open
|
Quarter Finals | Denis Shapovalov |
6-0
6-3 |
| 2019 |
Intrum Stockholm Open
|
1/8 | Denis Shapovalov |
6-4
7-6 |
| 2019 |
Shanghai Rolex Masters
|
1/16 | Novak Djokovic |
6-3
6-3 |
| 2019 |
Shanghai Rolex Masters
|
1/32 | Denis Shapovalov |
4-6
2-6 |
