Stadium: Hard 17 Round: 28 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/03 10:20 | Guy Den Heijer v Enrico Dalla Valle | 2-6,1-6 |
| 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 |
| ITF M25 Heraklion | 2023/11/03 08:00 | Guy Den Ouden v Vladyslav Orlov | 6-4,1-6,6-1 |
| ITF M25 Heraklion | 2023/11/02 10:00 | Guy Den Ouden v Szymon Kielan | 7-5,6-0 |
| ITF M25 Heraklion | 2023/11/01 11:55 | Guy Den Ouden v Benjamin Pietri | 2-6,6-3,6-2 |
| ITF M15 Heraklion | 2023/10/27 07:00 | Guy Den Ouden v Adam Heinonen | 6-7,6-1,2-6 |
| ITF M15 Heraklion | 2023/10/25 06:30 | Guy Den Ouden v Ioannis Kountourakis | 7-5,6-4 |
| ITF M15 Heraklion | 2023/10/20 07:00 | Guy Den Ouden v Jakub Nicod | 2-6,6-7 |
| ITF M15 Heraklion | 2023/10/19 08:45 | Dax Donders v Guy Den Ouden | 6-7,5-7 |
| ITF M15 Heraklion | 2023/10/18 07:25 | Guy Den Ouden v Matthew William Donald | 6-4,6-2 |