Stadium: Court 6 Round: 54 Ground: Hardcourt outdoor
| ITF M25 - Roehampton | 2023/07/17 09:50 | Luke Simkiss v Ryan James Storrie | 5-7,2-6 |
| ITF M25 - Roehampton | 2023/07/16 10:00 | Alexander Klintcharov v Luke Simkiss | 4-6,5-7 |
| 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 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 M25 - Grasse | 2023/06/11 15:35 | Cosme Rolland De Ravel v Zach Stephens | 6-1,6-1 |
| ITF - M25 La Nucia | 2023/06/01 07:00 | Valentin Royer v Zach Stephens | 6-2,6-2 |
| ITF - M25 Mataro | 2023/05/23 14:55 | Zach Stephens v Nikolas Sanchez Izquierdo | 1-6,1-6 |
| ITF - M25 Valldoreix | 2023/05/10 09:30 | Javier Barranco Cosano v Zach Stephens | 6-1,6-2 |
| ITF - M25 Sabadell | 2023/04/30 07:00 | Zach Stephens v Gianni Ross | 2-6,2-6 |
| ITF M15 - Telde | 2023/04/18 11:55 | Zach Stephens v Xavi Matas Ortega | 2-6,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2023/03/29 10:50 | Zach Stephens v Zura Tkemaladze | 4-6,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2023/03/22 10:00 | Tuncay Duran v Zach Stephens | 6-2,6-2 |