Stadium: Court 2 Round: 25 Ground: Clay
| ITF M25 Heraklion | 2022/11/21 08:00 | Milan Drinic v Ioannis Kountourakis | 7-5,7-6 |
| 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 |
| ITF M15 Kursumlijska Banja | 2023/06/22 10:05 | Andrey Chepelev v Milan Drinic | 6-3,6-3 |
| ITF M15 Kursumlijska Banja | 2023/06/21 10:15 | Milan Drinic v Sasa Markovic | 3-6,6-3,6-4 |
| ITF M15 Metzingen | 2023/07/23 07:30 | Ioannis Kountourakis v Stepan Mruzek | 3-6,5-7 |
| ITF M15 Sofia | 2023/07/03 09:30 | Ioannis Kountourakis v Adam Heinonen | 6-7,5-7 |
| ITF M15 Sofia | 2023/07/02 11:00 | Ioannis Kountourakis v Daniele Minighini | 6-3,6-3 |
| ITF M15 Belgrade | 2023/06/26 10:00 | Maxence Rivet v Ioannis Kountourakis | 6-3,6-2 |
| ITF M15 Belgrade | 2023/06/25 07:00 | Stefan Micov v Ioannis Kountourakis | 6-4,3-6,8-10 |
| ITF M15 Heraklion | 2023/03/19 07:00 | Ioannis Kountourakis v Mark Neyelov | 3-6,3-6 |
| ITF M15 Sharm El Sheikh | 2023/02/20 09:00 | Ioannis Kountourakis v Ji Hoon Son | 3-6,1-6 |
| ITF M15 Sharm El Sheikh | 2023/02/19 11:30 | Ioannis Kountourakis v Ioan A Teglas | 6-3,7-5 |