Stadium: Court 1 Round: 62 Ground: Hardcourt outdoor
| ITF - M15 Sharm El Sheikh | 2023/12/10 09:30 | Thomas Gerbaud v Ruben Gospodjinacki | 6-0,6-4 |
| ITF - M15 Sharm El Sheikh | 2023/12/03 13:00 | Ruben Gospodjinacki v Darrshan Suresh | 4-6,6-1,4-10 |
| ITF - M15 Teherán | 2023/06/12 07:30 | Ruben Gospodjinacki v Manish Ganesh | 1-6,2-6 |
| ITF - M15 Pazardžik | 2023/05/22 07:00 | Ruben Gospodjinacki v Peetu Pohjola | 4-6,6-0,6-10 |
| ITF - M15 Pazardžik | 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 - M25 Heraklion | 2023/10/30 11:00 | Andrej Radojicic v Filippo Romano | 1-6,1-6 |
| ITF - M25 Heraklion | 2023/10/29 10:30 | Dominique Graf v Andrej Radojicic | 3-6,2-6 |
| ITF - M15 Heraklion | 2023/10/22 09:30 | Robert Guna v Andrej Radojicic | 6-1,6-2 |
| ITF - M15 Kuršumlijska Banja | 2023/09/20 07:25 | Viktor Jovic v Andrej Radojicic | 6-2,6-0 |
| ITF - M15 Kuršumlijska Banja | 2023/09/13 14:55 | Romeo Hadzimehmedovic v Andrej Radojicic | 3-6,6-3,6-1 |
| ITF - M15 Kuršumlijska Banja | 2023/08/30 08:55 | Andrej Radojicic v Luka Pavlovic | 3-6,3-6 |
| ITF - M25 Osijek | 2023/08/07 10:50 | Matic Dimic v Andrej Radojicic | 6-3,6-1 |
| ITF - M25 Osijek | 2023/08/06 07:30 | Ainur Garifullin v Andrej Radojicic | 0-6,4-6 |