| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Miami Open
|
1/32 | Dusan Lajovic |
2-6
6-2 6-3 |
| 2016 |
Swiss Indoors Basel
Switzerland, Basel |
1/16 | Kei Nishikori |
5-7
1-6 |
| 2014 |
Australian Open
Australia, Victoria, Melbourne |
1/32 | Kei Nishikori |
1-6
1-6 6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Mexican Open
|
1/16 | Dusan Lajovic |
7-6
4-6 3-6 |
| 2020 |
Rio Open
|
1/8 | Lorenzo Sonego |
7-6
7-6 |
| 2020 |
Rio Open
|
1/16 | Dusan Lajovic |
4-6
7-6 1-6 |
| 2020 |
Argentina Open
|
Quarter Finals | Casper Ruud |
7-5
6-1 |
| 2020 |
Argentina Open
|
1/8 | Dusan Lajovic |
6-7
6-7 |
| 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 |
