Stadium: Hard 20 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/09 09:35 | Enrico Dalla Valle v Harry Wendelken | 4-6,1-6 |
| 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 |
| ITF M25 Heraklion | 2023/11/08 07:00 | Guy Den Heijer v Mattia Ricci | 6-2,6-1 |
| ITF M25 Heraklion | 2023/11/07 07:30 | Guy Den Heijer v Simon Freund | 6-2,3-6,10-5 |
| ITF M25 Heraklion | 2023/11/06 07:00 | Guy Den Heijer v Evangelos Kypriotis | 6-1,7-5 |
| 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 | 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 |