Stadium: Court 1 Round: 25 Ground: Clay
| ITF - M25 Maribor | 2023/08/31 09:50 | Filip Cristian Jianu v Stefan Popovic | 5-7,4-6 |
| Challenger - Praga | 2023/08/21 11:50 | Lorenzo Giustino v Filip Cristian Jianu | 6-4,6-3 |
| ITF - M25 Ystad | 2023/08/18 10:00 | Marvin Moeller v Filip Cristian Jianu | 3-6,7-5,6-0 |
| ITF - M25 Ystad | 2023/08/17 10:45 | John Sperle v Filip Cristian Jianu | 4-6,2-6 |
| ITF - M25 Ystad | 2023/08/15 11:30 | Leonardo Catani v Filip Cristian Jianu | 2-6,0-6 |
| Challenger - Banja Luka | 2023/08/08 08:30 | Filip Cristian Jianu v Norbert Gombos | 6-7,2-6 |
| ITF - M25 Bacau | 2023/07/29 08:00 | Marius Copil v Filip Cristian Jianu | 6-7,6-3,6-2 |
| ITF - M25 Bacau | 2023/07/28 09:00 | Luca Giacomini v Filip Cristian Jianu | 7-6,4-6,3-6 |
| ITF - M15 Kursumlijska Banja | 2023/08/30 10:30 | Milan Drinic v Peter Fajta | 3-6,6-3,6-7 |
| ITF - M25 Osijek | 2023/08/10 09:45 | Milan Drinic v Sebastian Prechtel | 5-7,7-6,2-6 |
| ITF - M25 Osijek | 2023/08/08 10:55 | Viktor Jovic v Milan Drinic | 2-6,3-6 |
| ITF - M15 Novi Sad | 2023/08/01 11:10 | Kristijan Juhas v Milan Drinic | 6-3,1-6,13-11 |
| ITF - M15 Novi Sad | 2023/07/31 15:40 | Nini Gabriel Dica v Milan Drinic | 3-6,6-7 |
| ITF - M15 Novi Sad | 2023/07/30 08:30 | Aleksandar Mihailovic v Milan Drinic | 5-7,1-6 |
| ITF - M15 Novi Sad | 2023/07/24 13:10 | Milan Drinic v Shendrit Deari | 6-4,5-7,4-10 |
| ITF - M15 Belgrade | 2023/06/25 07:00 | Milan Drinic v Irakli Tsurtsumia | 6-0,3-6,14-16 |