Denis Shapovalov is one win away from reaching his first ever Grand Slam quarterfinal.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
BMW Open
|
1/8 | David Goffin |
5-7
6-3 6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Santo Domingo
|
1/16 | Thiago Monteiro |
6-2
6-2 |
| 2019 |
Santo Domingo
|
1/32 | Victor Estrella Burgos |
7-5
7-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Internazionali BNL d'Italia
|
1/16 | Marin Cilic |
6-2
6-2 |
| 2020 |
US Open ATP
|
1/8 | Denis Shapovalov |
6-7
6-3 6-4 6-3 |
| 2020 |
US Open ATP
|
1/16 | David Goffin |
1-6
6-7 4-6 |
| 2020 |
US Open ATP
|
1/32 | David Goffin |
6-7
6-4 1-6 4-6 |
| 2020 |
US Open ATP
|
1/64 | David Goffin |
6-7
6-3 1-6 4-6 |
| 2020 |
Western & Southern Open
|
1/8 | Jan-Lennard Struff |
6-4
3-6 6-4 |
| 2020 |
Western & Southern Open
|
1/16 | David Goffin |
6-7
4-6 |
