Stadium: Court 6 Round: 62 Ground: Clay
| 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 M15 Krsko | 2023/05/15 10:00 | Jan Dimitrijevic v Shunsuke Wakita | 4-6,6-4,10-4 |
| ITF M15 Osijek | 2023/04/30 09:30 | Daniele Minighini v Jan Dimitrijevic | 6-4,6-3 |
| ITF M25 Split | 2023/04/17 17:20 | Luka Miklavcic v Jan Dimitrijevic | 6-0,2-6,11-9 |
| ITF M25 Opatija | 2023/03/20 13:30 | Jan Dimitrijevic v Federico Marchetti | 1-6,1-6 |
| ITF M15 Eupen | 2023/08/07 13:00 | Kyle Overmyer v Victor Ernaelsteen | 7-6,4-6,5-10 |
| ITF M15 Lakewood | 2023/07/10 17:00 | Logan Zapp v Kyle Overmyer | 6-3,6-1 |
| ITF M15 Lakewood | 2023/07/04 17:00 | Maxwell McKennon v Kyle Overmyer | 6-3,6-2 |
| ITF M15 Lakewood | 2023/07/03 17:00 | Kyle Overmyer v Jelani Sarr | 5-7,6-4,10-6 |
| ITF M25 Mataro | 2023/05/22 10:30 | Stefanos Sakellaridis v Kyle Overmyer | 3-6,6-2,10-6 |
| ITF M25 Mataro | 2023/05/21 12:00 | Carlos Giraldi v Kyle Overmyer | 2-6,6-7 |
| ITF M25 Gurb | 2023/05/15 07:00 | Dali Blanch v Kyle Overmyer | 6-2,6-1 |
| ITF M25 Gurb | 2023/05/14 07:00 | Laurent Julia Calac v Kyle Overmyer | 2-6,4-6 |