Both Japanese players reached the final four at Flushing Meadows.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Miami Open
|
1/8 | Kei Nishikori |
3-6
6-4 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Biella
|
1/8 | Federico Delbonis |
3-6
5-7 |
| 2018 |
Biella
|
1/16 | Federico Delbonis |
6-3
3-6 1-6 |
| 2018 |
Genova
|
Semi Finals | Lorenzo Sonego |
5-7
3-6 |
| 2018 |
Genova
|
Quarter Finals | Federico Delbonis |
3-6
6-3 6-7 |
| 2018 |
Genova
|
1/16 | Federico Delbonis |
6-4
4-6 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Open de Moselle
|
1/8 | Kei Nishikori |
7-6
6-3 |
| 2018 |
US Open ATP
|
Semi Finals | Novak Djokovic |
3-6
4-6 2-6 |
| 2018 |
US Open ATP
|
Quarter Finals | Kei Nishikori |
6-2
4-6 6-7 6-4 4-6 |
| 2018 |
US Open ATP
|
1/8 | Kei Nishikori |
6-3
6-2 7-5 |
| 2018 |
US Open ATP
|
1/16 | Kei Nishikori |
4-6
4-6 7-5 1-6 |
| 2018 |
US Open ATP
|
1/32 | Kei Nishikori |
2-6
4-5 |
| 2018 |
US Open ATP
|
1/64 | Kei Nishikori |
2-6
2-6 3-6 |
| 2018 |
Western & Southern Open
|
1/16 | Stan Wawrinka |
4-6
4-6 |
| 2018 |
Western & Southern Open
|
1/32 | Kei Nishikori |
7-5
6-3 |
