| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
BNP Paribas Open
|
Championship | ||
| 2015 |
Citi Open
|
1/8 | Kei Nishikori |
4-6
4-6 |
| 2014 |
US Open
|
1/16 | Kei Nishikori |
6-4
6-2 6-3 |
| 2013 |
Wimbledon
|
1/32 | Kei Nishikori |
7-6
6-4 6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Chile Open
|
1/16 | Thiago Monteiro |
6-7
6-3 6-4 |
| 2020 |
Rio Open
|
1/16 | Lorenzo Sonego |
1-6
7-5 4-6 |
| 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 |
