Stadium: Court 4 Round: 44 Ground: Clay
| ITF - M15 Kursumlijska Banja | 2023/09/10 07:00 | Ioannis Kountourakis v Jordi Garcia Mestre | 6-1,6-0 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/04 07:30 | Ioannis Kountourakis v Lorenzo Vatteroni | 6-2,6-3 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/03 10:00 | Mal Agushi v Ioannis Kountourakis | 5-7,3-6 |
| ITF - M15 Kursumlijska Banja | 2023/08/31 11:20 | Ioannis Kountourakis v Dusan Obradovic | 4-6,6-7 |
| ITF - M15 Kursumlijska Banja | 2023/08/30 13:45 | Nikola Djosic v Ioannis Kountourakis | 4-6,7-6,1-6 |
| ITF - M15 Kursumlijska Banja | 2023/08/29 09:45 | Ioannis Kountourakis v Maxim Krapivin | 6-2,6-4 |
| ITF - M15 Kursumlijska Banja | 2023/08/28 12:00 | Lorenzo Vatteroni v Ioannis Kountourakis | 6-0,3-6,9-11 |
| ITF M15 Madrid | 2023/09/07 10:50 | Iamachkine, Pedro v Nicola Kuhn | 6-7,7-5,1-6 |
| ITF M15 Madrid | 2023/09/06 08:00 | Karim-Mohamed Maamoun v Iamachkine, Pedro | 6-2,3-6,2-6 |
| ITF M15 Madrid | 2023/09/05 10:00 | Iamachkine, Pedro v Ivan Kazakov | 6-2,6-3 |
| ITF M15 Madrid | 2023/09/04 10:00 | Iamachkine, Pedro v Pedro A De Almeida Santos | 6-3,3-6,10-4 |
| ITF M25 Oviedo | 2023/08/28 17:15 | Javier Molino v Iamachkine, Pedro | 4-6,7-6,10-8 |
| ITF M15 Xativa | 2023/07/31 07:00 | Borys Zgola v Iamachkine, Pedro | 6-7,6-3,10-6 |
| ITF M15 Xativa | 2023/07/30 07:00 | Rodrigo Mora Clement v Iamachkine, Pedro | 2-6,3-6 |
| ITF M25 Denia | 2023/07/23 14:30 | Iamachkine, Pedro v Nil Regas Luis | 2-6,6-1,4-10 |