Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/09/14 07:00 | Plamen Milushev v Samuil Konov | 6-4,6-3 |
| ITF M15 Sozopol | 2021/09/13 07:00 | Plamen Milushev v Nikola Kolyachev | 6-4,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 08:30 | Plamen Milushev v Dian Nedev | 4-6,2-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 12:00 | Iliyan Radulov v Plamen Milushev | 6-3,1-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 07:58 | Plamen Milushev v Dmitrii Vasilev | 6-1,6-0 |
| ITF M15 Sofia | 2021/07/05 07:00 | Plamen Milushev v Leonid Sheyngezikht | 3-6,6-3,9-11 |
| ITF M15 Sofia | 2021/07/04 07:30 | Andrea Picchione v Plamen Milushev | 6-7,0-6 |
| ITF M15 Telavi | 2021/08/03 08:05 | Timur Khabibulin v George Tsivadze | 6-1,6-2 |
| ITF M25 Telavi | 2021/07/30 08:25 | George Tsivadze v Julian Cash | 6-7,4-6 |
| ITF M15 Tbilisi | 2021/05/18 12:25 | Lorenzo Rottoli v George Tsivadze | 7-6,6-4 |
| ITF M15 Doha | 2020/03/11 13:55 | Razvan M Codescu v George Tsivadze | 1-6,0-6 |
| ITF M25 Aktobe | 2020/02/17 09:20 | George Tsivadze v Vladimir Osminkin | 6-2,3-6,4-10 |
| ITF M25 Aktobe | 2020/02/12 08:20 | Vladyslav Manafov v George Tsivadze | 6-3,6-3 |
| ITF M15 Doha | 2019/12/19 10:20 | George Tsivadze v Jonathan Mridha | 6-4,0-6,1-6 |
| ITF M15 Doha | 2019/12/18 15:50 | Niklas Johansson v George Tsivadze | 2-6,2-6 |