Despite 16 aces, Dimitrov failed to convert any of his three break-point chances.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2015 |
Orleans
|
Semi Finals | Jerzy Janowicz |
1-6
6-2 4-6 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2019 |
Nur-Sultan 2
|
Final | Illya Marchenko |
6-4
4-6 3-6 |
| 2019 |
Nur-Sultan 2
|
Semi Finals | Illya Marchenko |
1-6
7-6 6-4 |
| 2019 |
Nur-Sultan 2
|
Quarter Finals | Illya Marchenko |
6-4
6-3 |
| 2019 |
Nur-Sultan 2
|
1/8 | Illya Marchenko |
4-6
2-6 |
| 2019 |
Nur-Sultan 2
|
1/16 | Illya Marchenko |
6-4
6-3 |
| 2019 |
Nur-Sultan 2
|
1/32 | Illya Marchenko |
6-4
7-5 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2017 |
Bratislava
|
Quarter Finals | Mikhail Kukushkin |
3-6
7-6 4-0 |
| 2017 |
Bratislava
|
1/8 | Jerzy Janowicz |
6-7
6-7 |
| 2017 |
Bratislava
|
1/16 | Jerzy Janowicz |
3-6
7-5 7-6 |
| 2017 |
Eckental
|
Final | Maximilian Marterer |
6-7
6-3 3-6 |
| 2017 |
Eckental
|
Semi Finals | Jerzy Janowicz |
6-7
6-4 6-3 |
| 2017 |
Eckental
|
Quarter Finals | Jerzy Janowicz |
4-6
4-6 |
| 2017 |
Eckental
|
1/8 | Jerzy Janowicz |
6-7
3-6 |
| 2017 |
Eckental
|
1/16 | Jerzy Janowicz |
6-7
1-6 |
| 2017 |
Erste Bank Open, Qualification
|
1/8 | Guillermo Garcia-Lopez |
6-7
4-6 |
