Estadio: Court 7 Round: 19 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/09/11 07:00 | Antonio Massara v Luka Todorovic | 6-4,6-2 |
| ITF M15 Pirot | 2023/09/08 09:50 | Antonio Massara v Dusan Obradovic | 2-6,2-6 |
| ITF M15 Pirot | 2023/09/07 09:00 | Alen Mujakic v Antonio Massara | 4-6,1-6 |
| ITF M15 Pirot | 2023/09/06 11:00 | Marko Nikolic v Antonio Massara | 3-6,2-6 |
| ITF M15 Pirot | 2023/09/05 10:50 | Antonio Massara v Filiberto Fumagalli | 6-4,6-2 |
| ITF M15 Pirot | 2023/09/04 10:00 | Antonio Massara v Aleksandar Mihailovic | 6-3,6-1 |
| ITF M25 Padova | 2023/07/09 15:25 | Antonio Massara v Gian Marco Ortenzi | 6-3,6-7,3-10 |
| ITF M15 Sofía | 2023/07/05 08:50 | Antonio Massara v Simon A Ivanov | 6-7,6-2,3-6 |
| ITF M15 Kursumlijska Banja | 2023/09/11 09:30 | Ioannis Kountourakis v Pedro Iamachkine | 6-4,6-1 |
| ITF M15 Kursumlijska Banja | 2023/09/10 07:00 | Ioannis Kountourakis v Jordi Garcia Mestre | 6-1,6-0 |
| ITF M15 Pirot | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| ITF M15 Pirot | 2023/09/04 07:30 | Ioannis Kountourakis v Lorenzo Vatteroni | 6-2,6-3 |
| ITF M15 Pirot | 2023/09/03 10:00 | Mal Agushi v Ioannis Kountourakis | 5-7,3-6 |
| ITF M15 Kursumlijska Banja | 2023/08/31 11:20 | Ioannis Kountourakis v Dusan Obradovic | 4-6,6-7 |
| ITF M15 Kursumlijska Banja | 2023/08/30 13:45 | Nikola Djosic v Ioannis Kountourakis | 4-6,7-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/08/29 09:45 | Ioannis Kountourakis v Maxim Krapivin | 6-2,6-4 |