Stadium: Court 1 Round: 62 Ground: Clay
| ITF - M15 Kursumlijska Banja | 2023/08/28 12:00 | Lorenzo Vatteroni v Ioannis Kountourakis | 6-0,3-6,9-11 |
| ITF - M15 Metzingen | 2023/07/23 07:30 | Ioannis Kountourakis v Stepan Mruzek | 3-6,5-7 |
| ITF M15 Sofia | 2023/07/03 09:30 | Ioannis Kountourakis v Adam Heinonen | 6-7,5-7 |
| ITF M15 Sofia | 2023/07/02 11:00 | Ioannis Kountourakis v Daniele Minighini | 6-3,6-3 |
| ITF M15 - Belgrado | 2023/06/26 10:00 | Maxence Rivet v Ioannis Kountourakis | 6-3,6-2 |
| ITF M15 - Belgrado | 2023/06/25 07:00 | Stefan Micov v Ioannis Kountourakis | 6-4,3-6,8-10 |
| ITF - M15 Heraklion | 2023/03/19 07:00 | Ioannis Kountourakis v Mark Neyelov | 3-6,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2023/02/20 09:00 | Ioannis Kountourakis v Ji Hoon Son | 3-6,1-6 |
| ITF - M15 Kursumlijska Banja | 2023/08/28 12:00 | Shendrit Deari v Maxim Krapivin | 6-1,4-6,5-10 |
| ITF M15 - Novi Sad | 2023/08/01 07:30 | Maxim Krapivin v Aleksa Mardjonovic | 0-6,5-7 |
| ITF M15 - Novi Sad | 2023/07/30 08:30 | Andrej Radojicic v Maxim Krapivin | 2-6,3-6 |
| ITF M15 - Novi Sad | 2023/07/23 13:00 | Maxim Krapivin v Aljaz Jeran | 2-6,2-6 |
| ITF M15 - Belgrado | 2023/06/26 08:45 | Bogdan Pavel v Maxim Krapivin | 7-6,5-7,10-5 |
| ITF M15 - Belgrado | 2023/06/25 07:00 | Maxim Krapivin v Lazar Vojinovic | 6-4,3-6,10-8 |
| ITF - M15 Kursumlijska Banja | 2023/06/18 07:00 | Maxim Krapivin v Nicolas H Cuesta | 2-6,6-7 |
| ITF - M15 Kursumlijska Banja | 2023/06/13 07:00 | Sean Hess v Maxim Krapivin | 6-3,6-4 |