Despite 16 aces, Dimitrov failed to convert any of his three break-point chances.
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2014 |
Wimbledon
|
1/64 | Jerzy Janowicz |
4-6
6-3 6-3 3-6 6-3 |
| 2013 |
Australian Open
Australia, Victoria, Melbourne |
1/32 | Jerzy Janowicz |
7-6
6-3 1-6 0-6 5-7 |
| 2009 |
US Open, Qualification
|
Championship | Somdev Devvarman |
6-3
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 |
| year | Event | RND | Winner | Results |
|---|---|---|---|---|
| 2016 |
Indian Wells Masters, Qualification
|
1/24 (Special Qual) | Andrey Rublev |
6-3
2-6 5-7 |
| 2016 |
Abierto Mexicano Telcel, Qualification
|
1/8 | adrian menendez-maceiras |
1-6
5-7 |
| 2016 |
Delray Beach International Tennis Championships, Qualification
|
1/8 | Alejandro Falla |
5-7
6-2 6-1 |
