| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Brisbane International
|
Semi Finals | Kei Nishikori |
2-6
2-6 |
| 2017 |
Roland Garros
|
1/32 | Kei Nishikori |
3-6
0-6 6-7 |
| 2017 |
Australian Open
|
1/32 | Kei Nishikori |
3-6
4-6 3-6 |
| 2016 |
Open BancSabadell
|
1/8 | Kei Nishikori |
3-6
5-7 |
| 2015 |
BNP Paribas Masters
|
1/16 | Kei Nishikori |
7-6
6-7 6-1 |
| 2014 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Kei Nishikori |
6-4
6-2 |
| 2013 |
Internazionali BNL d'Italia
|
1/16 | Jeremy Chardy |
4-6
1-6 |
| 2012 |
Abierto Mexicano Telcel
Mexico, Acapulco |
1/8 | Jeremy Chardy |
1-6
7-6 6-0 |
| 2011 |
Sony Ericsson Open
United States, Florida, Miami |
Championship | Kei Nishikori |
6-7
2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Australian Open ATP
|
1/64 | David Goffin |
6-4
6-3 6-1 |
| 2020 |
Adelaide International
|
1/8 | Pablo Carreno Busta |
6-3
6-2 |
| 2020 |
Adelaide International
|
1/16 | Jeremy Chardy |
3-6
5-7 |
| 2020 |
Qatar Open
|
1/8 | Stan Wawrinka |
6-3
6-4 |
| 2020 |
Qatar Open
|
1/16 | Jeremy Chardy |
3-6
6-3 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 |
