Stadium: Court 4 Round: 14 Ground: Clay
| Challenger Parma | 2023/06/20 10:15 | Blaz Rola v Alexander Weis | 6-3,1-6,6-3 |
| Challenger Perugia | 2023/06/13 10:05 | Edoardo Lavagno v Alexander Weis | 6-3,7-6 |
| Challenger Perugia | 2023/06/12 10:10 | Alvaro Lopez San Martin v Alexander Weis | 6-3,6-7,6-7 |
| Challenger Perugia | 2023/06/11 11:55 | Giovanni Oradini v Alexander Weis | 1-6,4-6 |
| Challenger Vicenza | 2023/05/28 08:30 | Giovanni Fonio v Alexander Weis | 6-2,6-4 |
| Challenger Skopje | 2023/05/25 10:35 | Dragos Nicolae Madaras v Alexander Weis | 6-3,6-3 |
| Challenger Skopje | 2023/05/24 11:05 | Alexander Weis v Roman Andres Burruchaga | 6-4,6-0 |
| Challenger Skopje | 2023/05/22 11:45 | Alexander Weis v Marko Topo | 6-3,6-3 |
| ITF M15 Kursumlijska Banja | 2023/06/23 09:05 | Lautaro Midon v Federico Agustin Gomez | 1-6,4-6 |
| ITF M15 Kursumlijska Banja | 2023/06/22 10:35 | Sean Hess v Lautaro Midon | 1-6,0-6 |
| ITF M15 Kursumlijska Banja | 2023/06/21 08:50 | Lautaro Midon v Piotr Czaczkowski | 6-3,6-2 |
| ITF M15 Kursumlijska Banja | 2023/06/17 12:00 | Lautaro Midon v Gabriel Donev | 0-6,5-7 |
| ITF M15 Kursumlijska Banja | 2023/06/14 10:50 | Lautaro Midon v Marko Stakusic | 6-3,6-2 |
| ITF M25 Kursumlijska Banja | 2023/06/09 08:00 | Luka Pavlovic v Lautaro Midon | 7-6,6-0 |
| ITF M25 Kursumlijska Banja | 2023/06/08 10:05 | Lautaro Midon v Evgeny Tyurnev | 2-6,7-5,6-4 |
| ITF M25 Kursumlijska Banja | 2023/06/07 18:00 | Lautaro Midon v Niklas Schell | 6-3,6-4 |