Nishikori added, "I need many more matches to have confidence and [get] my tennis back."
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Roland Garros WTA
|
1/64 | Aryna Sabalenka |
7-5
6-1 |
| 2019 |
Italian Open
|
1/16 | Naomi Osaka |
6-3
6-3 |
| 2019 |
Italian Open
|
1/32 | Dominika Cibulkova |
2-6
3-6 |
| 2019 |
Madrid Open
|
1/32 | Naomi Osaka |
6-2
7-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Hamburg European Open
|
1/16 | Cristian Garin |
6-0
6-3 |
| 2020 |
Internazionali BNL d'Italia
|
1/32 | Kei Nishikori |
6-4
7-6 |
| 2020 |
Generali Open
|
1/16 | Miomir Kecmanovic |
4-6
6-4 6-2 |
