Stadium: Court 1 Round: 54 Ground: Clay
| ITF M15 Heraklion | 2019/05/29 07:00 | Martin Dimitrov v Erik Crepaldi | 5-7,4-6 |
| ITF M15 Heraklion | 2019/05/28 07:00 | Lukas Krainer v Martin Dimitrov | 4-6,4-6 |
| ITF M15 Heraklion | 2019/05/21 07:00 | Harry Meehan v Martin Dimitrov | 7-6,7-6 |
| ITF M15 Heraklion | 2019/05/20 07:00 | Sergey Shipilov v Martin Dimitrov | 6-7,3-6 |
| ITF M15 Heraklion | 2019/05/15 10:15 | Patrik Nema v Martin Dimitrov | 6-2,6-3 |
| ITF M15 Heraklion | 2019/05/14 07:00 | Romain Bauvy v Martin Dimitrov | 6-4,6-7,5-10 |
| ITF M15 Heraklion | 2019/05/13 09:00 | Harry Thursfield v Martin Dimitrov | 1-6,1-6 |
| ITF M15 Sozopol | 2019/05/08 10:10 | Martin Dimitrov v Petru-Alexandru Luncanu | 4-6,6-3,3-6 |
| ITF M15 Sozopol | 2019/05/09 07:00 | Plamen Milushev v Vasil Kirkov | 2-6,3-6 |
| ITF M15 Sozopol | 2019/05/07 10:00 | Plamen Milushev v Dian Nedev | 6-2,6-2 |
| ITF Turkey F38 | 2018/11/25 07:00 | Bjorn Nareyka v Plamen Milushev | 0-6,6-7 |
| ITF Turkey F37 | 2018/11/22 08:10 | Dejan Katic v Plamen Milushev | 4-6,6-4,6-3 |
| ITF Turkey F37 | 2018/11/21 07:00 | Plamen Milushev v Samuel Pointon | 6-0,6-3 |
| ITF Turkey F37 | 2018/11/19 11:45 | Maurizio Speziali v Plamen Milushev | 5-7,3-6 |
| ITF Turkey F37 | 2018/11/19 06:30 | Plamen Milushev v Cristian Florentin Voinea | 6-3,6-0 |
| ITF Turkey F36 | 2018/11/14 07:00 | Bruno Santanna v Plamen Milushev | 6-3,6-3 |