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 - M15 Kursumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/05 12:55 | Filip Cristian Jianu v Milan Drinic | 4-6,6-4,6-4 |
| 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 Prechtel, Sebastian | 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 | Dica , Nini Gabriel 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 Kursumlijska Banja | 2023/09/19 08:45 | Marko Nikolic v Ioannis Kountourakis | 4-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/18 11:00 | Aleksandar Mihailovic v Ioannis Kountourakis | 1-6,6-7 |
| ITF - M15 Kursumlijska Banja | 2023/09/13 11:35 | Vlad Andrei Dancu v Ioannis Kountourakis | 6-3,6-4 |
| ITF - M15 Kursumlijska Banja | 2023/09/12 07:00 | Antonio Massara v Ioannis Kountourakis | 6-7,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/11 09:30 | Ioannis Kountourakis v Iamachkine, Pedro | 6-4,6-1 |
| ITF - M15 Kursumlijska Banja | 2023/09/10 07:00 | Ioannis Kountourakis v Jordi Garcia Mestre | 6-1,6-0 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/04 07:30 | Ioannis Kountourakis v Lorenzo Vatteroni | 6-2,6-3 |