Stadium: Court 5 Round: 62 Ground: Clay
| ITF M15 Sofia | 2023/07/03 08:00 | Dmitrii Vasilev v Pourroy, Loris | 1-6,3-6 |
| ITF M15 Sofia | 2023/07/02 09:30 | Mal Agushi v Dmitrii Vasilev | 3-6,1-6 |
| ITF - M15 Kursumlijska Banja | 2023/06/18 07:00 | Martin Zeljenka v Dmitrii Vasilev | 6-3,6-4 |
| ITF - M15 Kursumlijska Banja | 2023/06/12 16:05 | Marko Stakusic v Dmitrii Vasilev | 6-1,6-2 |
| ITF - M15 Kursumlijska Banja | 2023/06/11 14:00 | Dmitrii Vasilev v Strahinja Musicki | 6-0,6-1 |
| ITF - M25 Kursumlijska Banja | 2023/06/05 07:00 | Alexander Zgirovsky v Dmitrii Vasilev | 6-3,6-2 |
| ITF - M25 Kursumlijska Banja | 2023/06/04 07:00 | Dmitrii Vasilev v Federico Hernan Giovanniello | 6-4,6-1 |
| ITF M15 Pazardzhik | 2023/05/22 07:00 | Vicente O Moratalla v Dmitrii Vasilev | 6-0,7-6 |
| ITF M15 Belgrade | 2023/06/25 09:30 | Puric, Nikola v Tadija Radovanovic | 6-4,3-6,10-7 |
| ITF - M15 Kursumlijska Banja | 2023/06/18 09:30 | Tadija Radovanovic v Tsurtsumia, Irakli | 3-6,7-6,7-10 |
| ITF - M15 Kursumlijska Banja | 2023/06/11 09:30 | Tadija Radovanovic v Khomich, Aleksei | 2-6,2-6 |
| ITF - M15 Kursumlijska Banja | 2023/05/28 11:00 | Tadija Radovanovic v Semen Voronin | 5-7,4-6 |
| ITF - M15 Brcko | 2023/05/22 07:30 | Tadija Radovanovic v Radomir Tomic | 2-6,2-6 |
| ITF - M15 Brcko | 2023/05/21 07:30 | Radovan Michalik v Tadija Radovanovic | 6-2,5-7,6-10 |
| ITF - M25 Kursumlijska Banja | 2023/05/17 12:25 | Miljan Zekic v Tadija Radovanovic | 6-1,6-1 |
| ITF - M25 Kursumlijska Banja | 2023/05/16 07:00 | Aleksandar Andic v Tadija Radovanovic | 3-6,2-6 |