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