Stadium: Court 3 Round: 45 Ground: Grass
| Challenger Surbiton | 2023/06/06 10:00 | Bu Yunchaokete v Harry Wendelken | 7-6,7-5 |
| Challenger Surbiton | 2023/06/05 10:00 | Pierre-Hugues Herbert v Harry Wendelken | 4-6,6-7 |
| Challenger Surbiton | 2023/06/04 12:25 | Harry Wendelken v Li Tu | 7-6,6-3 |
| ITF M15 Kalmar | 2023/05/16 12:45 | Harry Wendelken v Max Dahlin | 6-4,3-6,6-7 |
| ITF M25 Nottingham | 2023/05/04 14:05 | Daniil Glinka v Harry Wendelken | 6-2,6-2 |
| ITF M25 Nottingham | 2023/05/03 09:00 | Harry Wendelken v Sean Hodkin | 6-2,6-2 |
| ITF M25 Nottingham | 2023/04/25 12:40 | Harry Wendelken v Stuart Parker | 4-6,5-7 |
| ITF M25 Nottingham | 2023/04/18 09:00 | Mark Whitehouse v Harry Wendelken | 6-2,6-0 |
| Challenger Little Rock | 2023/06/01 16:00 | Alexis Galarneau v Alex Michelsen | 3-6,6-3,6-3 |
| Challenger Little Rock | 2023/05/30 20:25 | Alex Michelsen v Denis Yevseyev | 4-6,6-3,7-5 |
| Challenger Savannah | 2023/04/24 18:45 | Alex Michelsen v Patrick Kypson | 6-4,3-6,6-7 |
| Challenger Tallahassee | 2023/04/21 19:55 | Enzo Couacaud v Alex Michelsen | 7-5,7-5 |
| Challenger Tallahassee | 2023/04/20 16:30 | Lucas Pouille v Alex Michelsen | 3-6,5-7 |
| Challenger Tallahassee | 2023/04/18 15:00 | Alex Michelsen v Camilo Ugo Carabelli | 5-7,6-3,6-2 |
| ITF M25 Calabasas | 2023/03/26 19:30 | Alex Michelsen v Nathan Ponwith | 3-6,7-6,5-7 |
| ITF M25 Calabasas | 2023/03/25 19:50 | Alex Michelsen v Luke Saville | 6-2,6-1 |