| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
St. Petersburg Open
Russia, St. Petersburg |
Quarter Finals | Alexander Zverev |
6-2
6-2 |
| 2016 |
Wimbledon
England, Wimbledon |
1/32 | Alexander Zverev |
6-4
3-6 6-0 4-6 6-2 |
| 2016 |
Wimbledon
England, Wimbledon |
1/32 |
6-4
3-6 6-0 4-6 2-1 |
|
| 2014 |
bet-at-home Open - German Tennis Championships
|
1/16 | Alexander Zverev |
7-5
7-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Mexican Open
|
1/8 | Tommy Paul |
6-3
6-4 |
| 2020 |
Mexican Open
|
1/16 | Alexander Zverev |
6-7
1-6 |
| 2020 |
Australian Open ATP
|
Semi Finals | Dominic Thiem |
3-6
6-4 7-6 7-6 |
| 2020 |
Australian Open ATP
|
Quarter Finals | Alexander Zverev |
6-1
3-6 4-6 2-6 |
| 2020 |
Australian Open ATP
|
1/8 | Alexander Zverev |
4-6
4-6 4-6 |
| 2020 |
Australian Open ATP
|
1/16 | Alexander Zverev |
2-6
2-6 4-6 |
| 2020 |
Australian Open ATP
|
1/32 | Alexander Zverev |
6-7
4-6 5-7 |
| 2020 |
Australian Open ATP
|
1/64 | Alexander Zverev |
4-6
6-7 3-6 |
| 2020 |
ATP Cup, Group F
|
Championship | Denis Shapovalov |
2-6
2-6 |
| 2020 |
ATP Cup, Group F
|
Championship | Stefanos Tsitsipas |
1-6
4-6 |
| 2020 |
ATP Cup, Group F
|
Championship | Alex de Minaur |
6-4
6-7 2-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2018 |
St. Petersburg Open
|
1/8 | Roberto Bautista Agut |
6-7
6-3 3-6 |
| 2018 |
St. Petersburg Open
|
1/16 | Mikhail Youzhny |
6-7
4-6 |
| 2018 |
US Open ATP
|
1/64 | Marcos Baghdatis |
6-4
6-4 2-6 3-1 |
| 2018 |
Rogers Cup
|
1/16 | Robin Haase |
5-7
2-6 |
