Stadium: Campo 1 Round: 19 Ground: Clay
| Challenger Banja Luka | 2023/08/08 14:45 | Alex Molcan v Miljan Zekic | 6-1,6-2 |
| Challenger Banja Luka | 2023/08/07 16:00 | Miljan Zekic v Stefan Popovic | 6-3,6-0 |
| Challenger Banja Luka | 2023/08/07 12:45 | Miljan Zekic v Rrezart Cungu | 6-4,6-3 |
| Challenger Liberec | 2023/08/02 10:05 | Hernan Casanova v Miljan Zekic | 6-3,6-4 |
| Challenger Tampere | 2023/07/18 13:40 | Miljan Zekic v Mohamed Aziz Dougaz | 2-6,4-6 |
| Challenger Karlsruhe | 2023/07/04 14:00 | Miljan Zekic v Marko Topo | 3-6,4-6 |
| ITF M15 Belgrade | 2023/07/02 08:00 | Miljan Zekic v Ergi Kirkin | 6-3,5-7,3-6 |
| ITF M15 Belgrade | 2023/07/01 11:35 | Miljan Zekic v Andrey Chepelev | 7-6,7-5 |
| Challenger Cordenons | 2023/08/09 13:00 | Lukas Neumayer v Lorenzo Rottoli | 6-1,6-4 |
| Challenger Cordenons | 2023/08/08 11:05 | Lorenzo Rottoli v Roman Andres Burruchaga | 5-7,6-3,6-3 |
| Challenger Cordenons | 2023/08/07 14:15 | Sebastian Dominko v Lorenzo Rottoli | 3-6,5-7 |
| Challenger Cordenons | 2023/08/06 12:35 | Alessio Balestrieri v Lorenzo Rottoli | 0-6,5-7 |
| Challenger San Marino | 2023/07/31 09:00 | Valentin Vacherot v Lorenzo Rottoli | 6-3,6-4 |
| Challenger San Marino | 2023/07/30 08:00 | Francesco Giorgetti v Lorenzo Rottoli | 5-7,2-6 |
| Challenger Verona | 2023/07/23 10:25 | Lorenzo Rottoli v Giovanni Oradini | 6-7,1-6 |
| Challenger Tampere | 2023/07/18 11:30 | Daniel Rincon v Lorenzo Rottoli | 6-2,3-6,7-5 |