Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| 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 Turkey F36 | 2018/11/11 07:00 | Plamen Milushev v Samuel Pointon | 6-1,6-2 |
| ITF M15 Tucson | 2019/02/13 17:40 | Vasil Kirkov v Julian Bradley | 7-6,7-5 |
| ITF Canada F7 | 2018/09/11 20:55 | Vasil Kirkov v Michael Zhu | 2-6,3-6 |
| ITF Canada F6 | 2018/09/04 16:45 | Vasil Kirkov v Hiroyasu Ehara | 5-7,0-6 |
| ITF USA F23 | 2018/08/17 16:20 | Vasil Kirkov v Andrew Harris | 3-6,6-1,4-6 |
| ITF USA F23 | 2018/08/15 18:35 | Vasil Kirkov v Alan Kohen | 7-5,6-3 |
| ITF USA F22 | 2018/08/08 18:30 | Santiago Rodriguez Taverna v Vasil Kirkov | 3-6,6-3,6-4 |
| ITF USA F22 Qual | 2018/08/06 13:30 | Vasil Kirkov v Gage Brymer | 7-6,6-4 |
| ITF USA F22 Qual | 2018/08/05 14:30 | Vasil Kirkov v Sid Donarski | 6-3,6-2 |