Denis Shapovalov is one win away from reaching his first ever Grand Slam quarterfinal.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
Monterrey Open
|
1/16 | Monica Puig |
0-6
3-6 |
| 2014 |
Pattaya Open, Qualification
|
1/8 | Olga Savchuk |
6-4
4-6 5-7 |
| 2014 |
Australian Open, Qualification WTA
|
1/48 (Special Qual) | Alexandra Dulgheru |
6-3
3-6 6-0 |
| 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 |
