Stadium: Court 2 Round: 44 Ground: Clay
| ITF - M25 Kursumlijska Banja | 2023/06/06 07:00 | Alexander Zgirovsky v Gabriel Matuszewski | 6-4,6-3 |
| ITF - M25 Kursumlijska Banja | 2023/06/05 06:55 | Marko Nikolic v Gabriel Matuszewski | 3-6,6-2,6-10 |
| ITF - M15 Kursumlijska Banja | 2023/05/29 12:20 | Gabriel Matuszewski v Lorenzo Carboni | 1-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/05/28 11:00 | Gabriel Matuszewski v Benjamin Denis Alarcon | 6-3,6-7,10-3 |
| ITF M25 Opatija | 2023/03/19 10:30 | Jan Dimitrijevic v Gabriel Matuszewski | 6-3,6-3 |
| ITF - M15 Rovinj | 2023/03/13 09:00 | Jan Kupcic v Gabriel Matuszewski | 6-2,4-6,10-8 |
| ITF - M15 Rovinj | 2023/03/12 09:00 | Gabriel Matuszewski v Pietro Pampanin | 6-1,6-2 |
| ITF - M15 Porec | 2023/03/05 11:30 | Gabriel Matuszewski v Paul Valsecchi | 2-6,2-6 |
| ITF - M25 Kursumlijska Banja | 2023/05/10 13:45 | Mohamed Safwat v Marko Maksimovic | 6-3,7-6 |
| ITF - M15 Kursumlijska Banja | 2023/05/02 07:00 | Bertuccioli, Federico v Marko Maksimovic | 6-2,4-6,11-9 |
| ITF - M15 Kursumlijska Banja | 2023/05/01 08:00 | Marko Maksimovic v Geni Inoue | 6-3,6-1 |
| ITF - M15 Kursumlijska Banja | 2023/04/30 11:00 | Lazar Danic v Marko Maksimovic | 1-6,1-6 |
| ITF - M15 Kursumlijska Banja | 2023/04/26 09:20 | Marko Maksimovic v Gergely Madarasz | 2-6,1-6 |
| ITF - M15 Kursumlijska Banja | 2023/04/25 09:00 | Sergei Pogosian v Marko Maksimovic | 3-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/04/24 11:10 | Marko Maksimovic v Valerio Perruzza | 6-3,6-2 |
| ITF - M15 Kursumlijska Banja | 2023/04/23 13:30 | Strahinja Cejovic v Marko Maksimovic | 0-6,0-6 |