| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Wimbledon ATP
|
1/16 | Kei Nishikori |
6-4
6-3 6-2 |
| 2016 |
Indian Wells Masters
|
1/16 | Kei Nishikori |
6-7
6-7 |
| 2015 |
Australian Open
|
1/16 | Kei Nishikori |
7-6
1-6 2-6 3-6 |
| 2015 |
Brisbane International
|
1/8 | Kei Nishikori |
4-6
5-7 |
| 2014 |
Gerry Weber Open
|
Quarter Finals | Kei Nishikori |
1-6
6-7 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Las Vegas
|
Quarter Finals | Ernesto Escobedo |
4-6
7-6 6-7 |
| 2019 |
Fairfield
|
Final | Christopher O'connell |
4-6
4-6 |
| 2019 |
Fairfield
|
Quarter Finals | Steve Johnson |
6-1
6-1 |
| 2019 |
Fairfield
|
1/8 | Steve Johnson |
6-3
6-2 |
| 2019 |
Fairfield
|
1/16 | Steve Johnson |
7-6
6-4 |
| 2019 |
Rakuten Japan Open Tennis Championships, Qualification
|
1/8 | Yasutaka Uchiyama |
6-3
6-3 |
| 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 |
