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