| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
US Open ATP
|
Quarter Finals | Kei Nishikori |
6-2
4-6 6-7 6-4 4-6 |
| 2018 |
Monte Carlo Masters
|
Quarter Finals | Kei Nishikori |
6-4
6-7 6-3 |
| 2016 |
Barclays ATP World Tour Finals, Group John McEnroe
|
Championship | Marin Cilic |
6-3
2-6 3-6 |
| 2016 |
Swiss Indoors Basel
Switzerland, Basel |
Final | Marin Cilic |
6-1
7-6 |
| 2016 |
Wimbledon
England, Wimbledon |
1/8 | Marin Cilic |
6-1
5-1 |
| 2015 |
Rakuten Japan Open Tennis Championships
|
Quarter Finals | Kei Nishikori |
6-3
5-7 3-6 |
| 2015 |
Citi Open
|
Semi Finals | Kei Nishikori |
6-3
1-6 4-6 |
| 2014 |
US Open
|
Final | Marin Cilic |
3-6
3-6 3-6 |
| 2014 |
Open BancSabadell
|
Quarter Finals | Kei Nishikori |
1-6
3-6 |
| 2014 |
Brisbane International
|
Quarter Finals | Kei Nishikori |
4-6
7-5 2-6 |
| 2013 |
U.S. National Indoor Tennis Championships
|
Quarter Finals | Kei Nishikori |
4-6
2-6 |
| 2012 |
US Open
|
1/16 | Marin Cilic |
6-3
6-4 6-7 6-3 |
| 2011 |
Aircel Chennai Open
India, Chennai |
Championship | Kei Nishikori |
4-6
7-6 6-2 |
| 2010 |
US Open
United States, New York, Flushing Meadows |
Championship | Kei Nishikori |
5-7
7-6 3-6 7-6 6-1 |
| 2008 |
BNP Paribas Open
|
Championship | Marin Cilic |
2-6
4-6 |
| 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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Adria Tour, Group B
|
Championship | Danilo Petrovic |
2-4
2-4 |
| 2020 |
Adria Tour, Group B
|
Championship | Alexander Zverev |
4-3
0-4 4-3 |
| 2020 |
Adria Tour, Group B
|
Championship | Andrey Rublev |
4-3
2-4 4-1 |
| 2020 |
Davis Cup Qualifying Round
|
Championship | Marin Cilic |
7-6
7-6 |
| 2020 |
Dubai Tennis Championships
|
1/16 | Benoit Paire |
6-2
5-7 6-7 |
