Meanwhile, Medvedev and Rublev both fell in the third quarter of the Australian Open draw.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
Monte Carlo Masters
|
1/32 | Kei Nishikori |
4-6
6-2 6-1 |
| 2015 |
Barclays ATP World Tour Finals, Group Stan Smith
|
Championship | Kei Nishikori |
5-7
6-3 3-6 |
| 2012 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Kei Nishikori |
7-5
6-4 |
| 2012 |
Monte Carlo Rolex Masters
Monaco, Monte Carlo |
1/8 | Tomas Berdych |
6-2
2-6 4-6 |
| 2011 |
Swiss Indoors Basel
|
Championship | Kei Nishikori |
6-3
3-6 2-6 |
| 2011 |
Open BancSabadell
|
Championship | ||
| 2009 |
Brisbane International
Australia, Brisbane |
Championship | Kei Nishikori |
7-6
6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
US Open ATP
|
1/64 | Jenson Brooksby |
1-6
6-2 4-6 4-6 |
| 2019 |
Winston-Salem Open
|
1/16 | Filip Krajinovic |
3-6
7-5 6-1 |
| 2019 |
Winston-Salem Open
|
1/32 | Tomas Berdych |
6-1
3-6 6-3 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2021 |
Rotterdam Open
|
Quarter Finals | Borna Coric |
7-6
7-6 |
| 2021 |
Rotterdam Open
|
1/8 | Kei Nishikori |
3-6
6-2 5-7 |
| 2021 |
Rotterdam Open
|
1/16 | Kei Nishikori |
7-6
6-1 |
| 2021 |
Australian Open ATP
|
1/64 | Pablo Carreno Busta |
5-7
6-7 2-6 |
