| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Gerry Weber Open
Germany, Halle |
1/8 | Florian Mayer | |
| 2011 |
Australian Open
Australia, Victoria, Melbourne |
Championship | Kei Nishikori |
4-6
3-6 6-0 3-6 |
| 2008 |
Delray Beach International Tennis Championships
United States, Florida, Delray Beach |
Championship | Kei Nishikori |
0-6
3-4 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
US Open ATP
|
1/64 | Borna Coric |
6-2
6-2 5-7 6-4 |
| 2018 |
German Tennis Championships
|
1/16 | Pablo Carreno Busta |
2-6
6-1 7-6 |
