| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Western & Southern Open
|
1/32 | Ivo Karlovic |
4-6
7-6 3-6 |
| 2011 |
BNP Paribas Open
United States, California, Indian Wells |
Championship | Ivo Karlovic |
3-6
3-6 |
| 2008 |
Mutua Madrilena Masters Madrid
Spain, Madrid |
Championship | Gilles Simon |
6-7
6-4 6-7 |
| 2007 |
Nottingham Open
|
Championship | Ivo Karlovic |
7-6
6-7 6-4 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
European Open
|
1/16 | Gilles Simon |
6-1
6-2 |
| 2019 |
Shanghai Rolex Masters
|
1/32 | Cameron Norrie |
7-5
6-2 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/8 | Reilly Opelka |
7-6
7-6 |
| 2019 |
Rakuten Japan Open Tennis Championships
|
1/16 | Gilles Simon |
4-6
0-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
VTB Kremlin Cup
|
1/16 | Ivo Karlovic |
6-4
6-7 7-6 |
| 2019 |
US Open ATP
|
1/64 | Frances Tiafoe |
2-6
3-6 2-1 |
| 2019 |
Western & Southern Open
|
1/32 | Jan-Lennard Struff |
5-7
6-7 |
