Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Roehampton | 2023/08/07 12:00 | Emile Hudd v Michael Shaw | 3-6,6-3,4-10 |
| ITF M25 Roehampton | 2023/08/06 10:25 | Zach Stephens v Michael Shaw | 4-6,7-6,11-13 |
| ITF M25 Roehampton | 2023/08/01 12:25 | Michael Shaw v Patrick Brady | 3-6,5-7 |
| ITF M25 Roehampton | 2023/07/31 12:05 | Corey Gaal v Michael Shaw | 4-6,2-6 |
| ITF M25 Roehampton | 2023/07/30 09:00 | Freddy Blaydes v Michael Shaw | 3-6,4-6 |
| ITF M25 Roehampton | 2023/07/16 10:00 | Ryan James Storrie v Michael Shaw | 7-6,7-6 |
| ITF M25 Nottingham | 2023/07/10 10:00 | Massimo Giunta v Michael Shaw | 7-5,6-3 |
| ITF M25 Nottingham | 2023/07/09 10:00 | Thijmen Loof v Michael Shaw | 5-7,2-6 |
| 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 |
| Challenger Nottingham | 2023/06/11 15:40 | Harry Wendelken v Alex Michelsen | 6-4,3-6,5-7 |
| 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 |