Stadium: Court 3 Round: 27 Ground: Clay
| 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 Sofia | 2023/07/05 08:50 | Antonio Massara v Simon A Ivanov | 6-7,6-2,3-6 |
| ITF - M15 Sofia | 2023/07/03 11:30 | Viktor Jovic v Antonio Massara | 6-4,4-6,7-10 |
| ITF - M15 Sofia | 2023/07/03 06:30 | Nikola Kolyachev v Antonio Massara | 3-6,7-6,12-14 |
| ITF - M15 Pirot | 2023/09/07 07:30 | Francesco Ferrari v Dusan Obradovic | 1-6,2-6 |
| ITF - M15 Pirot | 2023/09/06 07:30 | Petr Bar Biryukov v Dusan Obradovic | 6-7,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/03 10:50 | Dusan Obradovic v Luka Pavlovic | 2-6,2-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/02 08:00 | Dusan Obradovic v Giannicola Misasi | 6-1,6-1 |
| ITF - M15 Kursumlijska Banja | 2023/09/01 10:00 | Emile Hudd v Dusan Obradovic | 4-6,5-7 |
| 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 14:45 | Mihail Ivanov v Dusan Obradovic | 2-6,3-6 |
| ITF - M25 Osijek | 2023/08/11 10:40 | Luka Mikrut v Dusan Obradovic | 7-6,6-3 |