Stadium: Court 3 Round: 62 Ground: Clay
| ITF M15 Kursumlijska Banja | 2024/07/15 09:00 | Aleksa Pisaric v Plamen Milushev | 3-6,5-7 |
| ITF M15 Kursumlijska Banja | 2024/07/14 09:00 | Nicolo Consonni v Plamen Milushev | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2024/05/22 06:55 | Diego A B Sanchez v Plamen Milushev | 6-2,6-1 |
| ITF M15 Kursumlijska Banja | 2024/05/21 06:30 | Saveliy Ivanov v Plamen Milushev | 0-6,3-6 |
| ITF M15 Kursumlijska Banja | 2024/05/20 14:30 | Marko Nikolic v Plamen Milushev | 4-6,6-7 |
| ITF M25 Pazardzhik | 2023/10/05 10:25 | Damien Wenger v Plamen Milushev | 6-2,6-1 |
| ITF M25 Pazardzhik | 2023/10/04 10:15 | Jasza Szajrych v Plamen Milushev | 6-3,6-7,5-7 |
| ITF M25 Pazardzhik | 2023/10/02 13:15 | Plamen Milushev v Maxwell Benson | 6-4,7-5 |
| ITF M15 Kursumlijska Banja | 2024/07/15 06:00 | Matej Djokic v Dinko Dinev | 1-6,2-6 |
| UTR Pro Skopje | 2024/07/08 08:30 | Dinko Dinev v Nikola Jovic | 2-6,0-0 |
| UTR Pro Skopje | 2024/07/06 07:00 | Andras Necz v Dinko Dinev | 6-1,6-0 |
| UTR Pro Skopje | 2024/07/04 10:31 | Dinko Dinev v Gabriel Alejandro Hidalgo | 6-7,3-6 |
| UTR Pro Skopje | 2024/07/02 07:00 | Dinko Dinev v Shendrit Deari | 6-1,6-4 |
| UTR Pro Skopje | 2024/07/01 09:25 | Dinko Dinev v Victor Sklenka | 6-7,1-5 |
| ITF M15 Kursumlijska Banja | 2024/06/17 12:00 | Dinko Dinev v Viktor Markov | 3-6,3-6 |
| ITF M15 Kursumlijska Banja | 2024/06/14 07:00 | Dinko Dinev v Luka Pavlovic | 7-5,2-6,2-6 |