Stadium: Center Court Round: 62 Ground: Hardcourt outdoor
| ITF M15 Tehran | 2023/06/12 07:30 | Ruben Gospodjinacki v Manish Ganesh | 1-6,2-6 |
| ITF M15 Pazardzhik | 2023/05/22 07:00 | Ruben Gospodjinacki v Peetu Pohjola | 4-6,6-0,6-10 |
| ITF M15 Pazardzhik | 2023/05/21 11:00 | Ivan Penev v Ruben Gospodjinacki | 5-7,0-6 |
| ITF M15 Antalya | 2023/05/14 12:00 | Ruben Gospodjinacki v Aleksander Chayka | 2-6,4-6 |
| ITF M15 Antalya | 2023/05/08 09:15 | Alexandr Binda v Ruben Gospodjinacki | 6-4,6-3 |
| ITF M15 Antalya | 2023/05/07 07:00 | Ivan Zaytsev v Ruben Gospodjinacki | 6-1,6-3 |
| ITF M15 Antalya | 2023/04/24 13:15 | Daniel Ibragimov v Ruben Gospodjinacki | 6-3,6-2 |
| ITF M15 Antalya | 2023/04/23 07:00 | Ruben Gospodjinacki v Imran Sibille | 7-6,6-3 |
| ITF M25 Sharm El Sheikh | 2023/11/06 13:05 | Alexander Krylov v Aljaz Jeran | 3-6,4-6 |
| ITF M25 Sharm El Sheikh | 2023/11/05 08:00 | Yi Ke Li v Alexander Krylov | 3-6,3-6 |
| ITF M15 Sharm El Sheikh | 2023/10/22 08:15 | Alexander Krylov v Thorben Sannen | 6-3,5-7,7-10 |