Estádio: Court 10 Round: 26 Ground: Hardcourt outdoor
| ITF - M25 Sintra | 2023/09/06 11:20 | Harry Wendelken v Jake Van Emburgh | 6-3,6-4 |
| ITF - M25 Idanha-a-Nova | 2023/08/31 09:55 | Johannes Ingildsen v Harry Wendelken | 7-5,6-0 |
| ITF - M25 Idanha-a-Nova | 2023/08/29 08:00 | Sergio Davila Godoy v Harry Wendelken | 0-6,5-7 |
| ITF - M25 Aldershot | 2023/08/16 09:00 | Harry Wendelken v Sean Hodkin | 4-6,4-6 |
| ITF - M25 Roehampton | 2023/08/10 09:30 | Michael Shaw v Harry Wendelken | 6-1,3-6,6-3 |
| ITF - M25 Roehampton | 2023/08/08 12:05 | Ryan James Storrie v Harry Wendelken | 2-6,7-6,4-6 |
| Wimbledon | 2023/06/26 10:00 | Matteo Gigante v Harry Wendelken | 6-3,7-6 |
| Challenger - Ilkley | 2023/06/20 10:30 | Sho Shimabukuro v Harry Wendelken | 6-2,6-7,6-2 |
| ITF - M25 Sintra | 2023/09/06 10:50 | Diego F Flores v Peter Sychev | 6-3,6-1 |
| ITF - M15 Monastir | 2023/08/17 08:30 | Etienne Donnet v Diego F Flores | 3-6,7-5,6-4 |
| ITF - M15 Monastir | 2023/08/16 08:30 | Diego F Flores v Dev Javia | 6-1,6-3 |
| ITF - M15 Monastir | 2023/08/09 11:00 | Gianluca Cadenasso v Diego F Flores | 2-6,6-4,5-7 |
| ITF - M25 Porto | 2023/07/26 14:15 | Diego F Flores v Joao Domingues | 5-7,4-6 |
| ITF - M25 Castelo Branco | 2023/07/21 10:40 | Jaime Faria v Diego F Flores | 6-3,6-2 |
| ITF - M25 Castelo Branco | 2023/07/20 08:30 | Diego F Flores v Sascha Gueymard Wayenburg | 6-2,1-6,6-4 |
| ITF - M25 Castelo Branco | 2023/07/19 11:05 | Raphael Lambling v Diego F Flores | 6-2,6-7,4-6 |