Stadium: Court 6 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Roehampton | 2023/08/10 09:30 | Charles Broom v Jack Pinnington Jones | 3-6,6-0,4-6 |
| ITF M25 Roehampton | 2023/08/08 10:00 | Finn Bass v Jack Pinnington Jones | 0-6,6-7 |
| ITF M25 Roehampton | 2023/08/02 10:00 | Jack Pinnington Jones v Paul Jubb | 4-6,5-7 |
| ITF M25 Roehampton | 2023/08/01 09:00 | Finn Murgett v Jack Pinnington Jones | 3-6,3-6 |
| ITF M25 Roehampton | 2023/07/18 11:35 | Jack Pinnington Jones v Patrick Brady | 6-3,5-7,3-6 |
| ITF M25 Nottingham | 2023/07/13 11:30 | Jack Pinnington Jones v Charles Broom | 6-4,4-6,0-6 |
| ITF M25 Nottingham | 2023/07/12 12:45 | Jack Pinnington Jones v Luke Simkiss | 4-6,6-3,6-4 |
| ITF M25 Nottingham | 2023/07/11 13:55 | Antoine Bellier v Jack Pinnington Jones | 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 | 2023/08/07 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 |