| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Argentina Open
|
Final | Alexandr Dolgopolov |
6-7
4-6 |
| 2016 |
Open BancSabadell
|
Quarter Finals | Kei Nishikori |
5-7
0-6 |
| 2016 |
Miami Open
|
1/16 | Kei Nishikori |
6-2
6-2 |
| 2015 |
Abierto Mexicano Telcel
|
Quarter Finals | Kei Nishikori |
6-4
6-4 |
| 2013 |
Brisbane International
Australia, Brisbane |
Quarter Finals | Kei Nishikori |
4-6
6-7 |
| 2011 |
Shanghai Rolex Masters
China, Shanghai |
Championship | Kei Nishikori |
4-6
3-6 |
| 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 |
| 2019 |
Rogers Cup
|
1/16 | Richard Gasquet |
6-7
6-2 7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Internazionali BNL d'Italia
|
1/32 | Novak Djokovic |
6-1
6-3 |
