Stadium: Hard 17 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2023/10/25 06:30 | Guy Den Ouden v Ioannis Kountourakis | 7-5,6-4 |
| ITF - M15 Heraklion | 2023/10/19 06:30 | Ioannis Kountourakis v Sidane Pontjodikromo | 4-6,6-2,2-6 |
| ITF - M15 Heraklion | 2023/10/18 08:10 | Ki Lung NG v Ioannis Kountourakis | 3-6,3-6 |
| ITF - M15 Heraklion | 2023/10/17 06:30 | Ioannis Kountourakis v Gabriel Matuszewski | 6-3,6-0 |
| ITF - M15 Heraklion | 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 |
| Challenger - Ortisei | 2023/10/27 12:55 | Enrico Dalla Valle v Lukas Klein | 3-6,2-6 |
| Challenger - Ortisei | 2023/10/26 14:10 | Abedallah Shelbayh v Enrico Dalla Valle | 6-4,3-6,4-6 |
| Challenger - Ortisei | 2023/10/25 10:00 | Yaroslav Demin v Enrico Dalla Valle | 6-7,4-6 |
| Challenger - Lisabona | 2023/10/03 15:45 | Enrico Dalla Valle v Flavio Cobolli | 4-6,7-5,0-6 |
| Challenger - Lisabona | 2023/10/02 11:15 | Henri Laaksonen v Enrico Dalla Valle | 7-6,2-6,3-6 |
| Challenger - Lisabona | 2023/10/01 13:40 | Tim Handel v Enrico Dalla Valle | 4-6,2-6 |
| ITF - M25 Santa Margherita | 2023/09/30 09:00 | Gilles Arnaud Bailly v Enrico Dalla Valle | 6-1,6-2 |
| ITF - M25 Santa Margherita | 2023/09/29 09:00 | Enrico Dalla Valle v Kirill Kivattsev | 6-7,6-2,7-5 |