Estadio: Indoor 3 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Nottingham | 2023/07/11 13:55 | Antoine Bellier v Jack Pinnington Jones | 4-6,4-6 |
| ITF M25 Tulsa | 2023/06/22 18:30 | Alfredo Perez v Jack Pinnington Jones | 7-6,6-2 |
| ITF M25 Tulsa | 2023/06/21 15:40 | Jack Pinnington Jones v Colin Markes | 6-2,6-2 |
| ITF M25 Wichita | 2023/06/15 15:00 | Peter Bertran v Jack Pinnington Jones | 1-6,6-2,6-4 |
| ITF M25 Wichita | 2023/06/14 19:50 | Jack Pinnington Jones v Aidan Mayo | 3-6,6-1,6-4 |
| ITF M25 Bakersfield | 2023/03/15 23:20 | Jack Pinnington Jones v Yuta Shimizu | 6-3,4-6,3-6 |
| ATP Dallas | 2023/02/05 21:35 | Jack Pinnington Jones v Mitchell Krueger | 4-6,3-6 |
| Challenger de Cleveland | 2023/02/01 19:15 | Emilio Gomez v Jack Pinnington Jones | 6-2,3-6,6-2 |
| ITF M25 Nottingham | 2023/07/11 14:00 | Luke Simkiss v Ali Habib | 6-1,6-2 |
| ITF M25 Nottingham | 2023/07/10 10:00 | Luke Simkiss v George Houghton | 7-6,6-1 |
| ITF M25 Nottingham | 2023/07/09 12:20 | Ronald Hohmann v Luke Simkiss | 6-2,3-6,6-10 |
| ITF M15 Alkmaar | 2023/07/01 11:50 | Luke Simkiss v Sander Jong | 4-6,1-6 |
| ITF M15 Alkmaar | 2023/06/30 14:30 | Alec Deckers v Luke Simkiss | 6-7,6-4,4-6 |
| ITF M15 Alkmaar | 2023/06/29 10:55 | Luke Simkiss v Sidane Pontjodikromo | 6-3,7-5 |
| ITF M15 Alkmaar | 2023/06/28 13:55 | Luke Simkiss v Florian Broska | 6-7,6-4,7-6 |
| ITF M15 Alkmaar | 2023/06/25 10:00 | Luke Tollenaar v Luke Simkiss | 0-6,1-6 |