Estadio: Court 1 Round: 44 Ground: Clay
| ITF M25 Maribor | 2023/08/30 12:00 | Jan Dimitrijevic v Tino Kovacic | 2-6,4-6 |
| ITF M25 Maribor | 2023/08/29 09:30 | Csongor Hejjas v Jan Dimitrijevic | 3-6,4-6 |
| ITF M25 Maribor | 2023/08/28 08:00 | Tarik Sehovic v Jan Dimitrijevic | 0-6,0-6 |
| ITF M15 Kottingbrunn | 2023/08/13 12:00 | Jan Dimitrijevic v Kyle Overmyer | 3-6,3-6 |
| ITF M15 Celje | 2023/06/28 16:50 | Jan Dimitrijevic v Bor Artnak | 1-6,1-6 |
| ITF M15 Store | 2023/06/21 17:15 | Zak Talic v Jan Dimitrijevic | 6-1,6-1 |
| ITF M15 Litija | 2023/06/12 11:00 | Jan Dimitrijevic v Matteo Fondriest | 2-6,1-6 |
| ITF M15 Krsko | 2023/05/17 08:00 | Dominik Kellovsky v Jan Dimitrijevic | 6-3,6-2 |
| ITF M25 Maribor | 2023/08/28 15:30 | Raphael Calzi v Vid Mohar | 6-1,6-2 |
| ITF M15 Store | 2023/06/19 09:30 | Vid Mohar v Alexander Klintcharov | 0-6,1-6 |