The former No. 3 has a big-name coach in his corner with few points to defend this season.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Miami Open
|
1/8 | Kei Nishikori |
3-6
6-4 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Rio Open
|
1/8 | Albert Ramos-Vinolas |
6-3
5-7 3-6 |
| 2019 |
Rio Open
|
1/16 | Federico Delbonis |
3-6
5-7 |
| 2019 |
Argentina Open
|
1/16 | Jaume Munar |
6-2
2-6 6-1 |
| 2019 |
Cordoba Open
|
Semi Finals | Juan Ignacio Londero |
6-1
6-0 |
| 2019 |
Cordoba Open
|
Quarter Finals | Federico Delbonis |
7-5
6-4 |
| 2019 |
Cordoba Open
|
1/8 | Federico Delbonis |
6-7
6-2 6-2 |
| 2019 |
Cordoba Open
|
1/16 | Federico Delbonis |
4-6
7-6 3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Rotterdam Open
|
Semi Finals | Stan Wawrinka |
2-6
6-4 4-6 |
| 2019 |
Rotterdam Open
|
Quarter Finals | Kei Nishikori |
6-3
6-2 |
| 2019 |
Rotterdam Open
|
1/8 | Kei Nishikori |
6-1
6-4 |
| 2019 |
Rotterdam Open
|
1/16 | Kei Nishikori |
3-6
6-1 6-4 |
| 2019 |
Australian Open ATP
|
Quarter Finals | Novak Djokovic |
6-1
4-1 |
| 2019 |
Australian Open ATP
|
1/8 | Kei Nishikori |
7-6
6-4 6-7 4-6 6-7 |
| 2019 |
Australian Open ATP
|
1/16 | Kei Nishikori |
6-7
1-6 2-6 |
| 2019 |
Australian Open ATP
|
1/32 | Kei Nishikori |
3-6
6-7 7-5 7-5 6-7 |
| 2019 |
Australian Open ATP
|
1/64 | Kei Nishikori |
6-3
7-6 0-6 2-6 0-3 |
| 2019 |
Brisbane International
|
Final | Kei Nishikori |
4-6
6-3 2-6 |
| 2019 |
Brisbane International
|
Semi Finals | Kei Nishikori |
2-6
2-6 |
| 2019 |
Brisbane International
|
Quarter Finals | Kei Nishikori |
5-7
5-7 |
| 2019 |
Brisbane International
|
1/8 | Kei Nishikori |
5-7
2-6 |
