Stadium: Court 16 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/02 08:00 | Guy Den Heijer v Marlon Vankan | 6-3,7-5 |
| ITF M25 Heraklion | 2023/11/01 12:00 | Stefanos Sakellaridis v Guy Den Heijer | 7-5,3-6,6-7 |
| ITF M25 Heraklion | 2023/10/31 07:00 | Guy Den Heijer v Joshua Charlton | 6-4,7-5 |
| ITF M25 Heraklion | 2023/10/30 09:30 | Guy Den Heijer v Gabriel Matuszewski | 6-1,6-4 |
| ITF M15 Heraklion | 2023/10/25 08:55 | Mario G Fernandez v Guy Den Heijer | 6-1,6-3 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Guy Den Heijer v Joshua Charlton | 7-6,7-5 |
| ITF M15 Heraklion | 2023/10/23 10:30 | Guy Den Heijer v Vojtech Mares | 5-7,7-6,10-6 |
| ITF M15 Heraklion | 2023/10/19 08:45 | Guy Den Heijer v Gabriel Decamps | 2-6,4-6 |
| ITF M25 Heraklion | 2023/11/02 08:00 | Peter Heller v Enrico Dalla Valle | 3-6,3-6 |
| ITF M25 Heraklion | 2023/11/01 10:10 | Ioannis Kountourakis v Enrico Dalla Valle | 4-6,1-6 |
| 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 Lisbon | 2023/10/03 15:45 | Enrico Dalla Valle v Flavio Cobolli | 4-6,7-5,0-6 |
| Challenger Lisbon | 2023/10/02 11:15 | Henri Laaksonen v Enrico Dalla Valle | 7-6,2-6,3-6 |
| Challenger Lisbon | 2023/10/01 13:40 | Tim Handel v Enrico Dalla Valle | 4-6,2-6 |