Stadium: Hard 20 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/08 10:05 | Enrico Dalla Valle v Dax Donders | 6-3,6-2 |
| ITF M25 Heraklion | 2023/11/04 08:00 | Enrico Dalla Valle v Guy Den Ouden | 3-6,2-6 |
| 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 |
| ITF M25 Heraklion | 2023/11/08 08:45 | Harry Wendelken v Alexander Orlov | 2-6,7-6,7-5 |
| ITF M25 Sunderland | 2023/11/01 13:20 | Patrick Brady v Harry Wendelken | 6-7,6-3,6-2 |
| ITF M25 Glasgow | 2023/10/26 11:35 | Hamish Stewart v Harry Wendelken | 7-5,6-4 |
| ITF M25 Glasgow | 2023/10/24 09:00 | Phoenix Weir v Harry Wendelken | 1-6,4-6 |
| ITF M25 Edgbaston | 2023/10/17 11:50 | Milos Karol v Harry Wendelken | 6-2,6-4 |
| UK Pro League | 2023/10/07 11:30 | Harry Wendelken v Oscar Weightman | 6-0,0-6,10-5 |
| UK Pro League | 2023/10/06 11:30 | Giles Hussey v Harry Wendelken | 6-1,6-1 |
| UK Pro League | 2023/10/05 13:00 | Harry Wendelken v Hamish Stewart | 7-6,5-7,10-4 |