Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| 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 |
| ITF Turkey F36 | 2018/11/12 07:00 | Mate Voros v Plamen Milushev | 3-6,6-7 |
| ITF M15 Sozopol | 2019/05/08 10:55 | Nikolay Vylegzhanin v Vasil Kirkov | 2-6,3-6 |
| ITF M15 Cairo | 2019/05/02 09:35 | Arnaud Bovy v Vasil Kirkov | 6-2,6-3 |
| ITF M15 Cairo | 2019/05/01 08:00 | Tarun Anirudh Chilakalapudi v Vasil Kirkov | 1-6,0-6 |
| ITF M15 Sunrise | 2019/04/09 15:00 | Vasil Kirkov v Bastian Malla | 6-1,2-6,2-6 |
| ITF M15 Cancun | 2019/03/20 16:55 | Vasil Kirkov v Andrew Watson | 6-7,3-6 |
| ITF M15 Cancun | 2019/03/18 19:30 | Vasil Kirkov v Aaron Schmid | 6-2,6-1 |
| ITF M15 Cancun | 2019/03/18 16:00 | Vasil Kirkov v Ivan Endara | 7-5,7-5 |
| ITF M15 Arcadia | 2019/03/15 19:30 | Vasil Kirkov v Alan Kohen | 4-6,2-6 |