Stadium: Hard 17 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Heráklion | 2023/10/18 08:10 | Ki Lung NG v Ioannis Kountourakis | 3-6,3-6 |
| ITF M15 Heráklion | 2023/10/17 06:30 | Ioannis Kountourakis v Gabriel Matuszewski | 6-3,6-0 |
| ITF M15 Heráklion | 2023/10/16 09:00 | Ioannis Kountourakis v Piotr Siekanowicz | 6-3,6-0 |
| ITF M15 Kursumlijska Banja | 2023/09/21 12:30 | Ioannis Kountourakis v Stefan Popovic | 2-6,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/19 08:45 | Marko Nikolic v Ioannis Kountourakis | 4-6,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/18 11:00 | Aleksandar Mihailovic v Ioannis Kountourakis | 1-6,6-7 |
| ITF M15 Kursumlijska Banja | 2023/09/13 11:35 | Vlad Andrei Dancu v Ioannis Kountourakis | 6-3,6-4 |
| ITF M15 Heráklion | 2023/10/17 09:00 | Kevin Edengren v Sidane Pontjodikromo | 0-6,3-6 |
| ITF M25 Santa Margherita | 2023/09/25 12:00 | Sidane Pontjodikromo v Kirill Kivattsev | 6-4,0-6,3-6 |
| ITF M25 Santa Margherita | 2023/09/20 08:30 | Antonio Caruso v Sidane Pontjodikromo | 7-5,6-1 |
| ITF M25 Santa Margherita | 2023/09/18 13:00 | Niels Visker v Sidane Pontjodikromo | 7-5,4-6,2-6 |
| ITF M15 Haren | 2023/09/10 11:00 | Sidane Pontjodikromo v Thiemo De Bakker | 3-6,2-6 |
| ITF M15 Haren | 2023/09/09 11:35 | Stijn Pel v Sidane Pontjodikromo | 5-7,0-6 |
| ITF M15 Haren | 2023/09/08 14:10 | Sidane Pontjodikromo v Sander Jong | 6-4,6-1 |
| ITF M15 Haren | 2023/09/07 12:20 | Sidane Pontjodikromo v Justin Roberts | 3-6,6-3,6-3 |