Despite 16 aces, Dimitrov failed to convert any of his three break-point chances.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Eckental
|
1/8 | Jerzy Janowicz |
6-7
3-6 |
| 2012 |
Roland Garros, Qualification
|
1/16 | Igor Sijsling |
4-6
6-3 4-6 |
| 2012 |
Wolfsburg
|
Final | Igor Sijsling |
6-4
3-6 6-7 |
| 2011 |
Heilbronn
|
Championship | Jerzy Janowicz |
4-6
3-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Helsinki
|
1/32 | Jaroslav Pospisil |
7-5
6-2 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2020 |
Pau
|
Final | Ernests Gulbis |
3-6
4-6 |
| 2020 |
Pau
|
Semi Finals | Jerzy Janowicz |
4-6
7-6 6-7 |
| 2020 |
Pau
|
1/8 | Jerzy Janowicz |
6-4
6-7 6-3 |
| 2020 |
Pau
|
1/16 | Jerzy Janowicz |
4-6
4-6 |
| 2020 |
Pau
|
1/32 | Jerzy Janowicz |
4-6
5-7 |
| 2020 |
Quimper
|
1/16 | Quentin Halys |
