Stadium: Indoor 1 Round: 29 Ground: Hardcourt outdoor
| ITF M25 Roehampton | 2023/08/04 11:00 | Dan Added v Luke Simkiss | 4-6,6-1,3-6 |
| ITF M25 Roehampton | 2023/08/03 11:05 | Luke Simkiss v Joshua Goodger | 5-7,6-4,6-3 |
| ITF M25 Roehampton | 2023/08/02 13:00 | Corey Gaal v Luke Simkiss | 5-7,4-6 |
| ITF M25 Roehampton | 2023/08/01 11:55 | William Jansen v Luke Simkiss | 3-6,6-1,5-7 |
| ITF M25 Roehampton | 2023/07/31 09:00 | Luke Simkiss v Emile Hudd | 7-5,7-6 |
| ITF M25 Roehampton | 2023/07/30 09:00 | Luke Simkiss v Zach Stephens | 6-4,7-5 |
| 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 Roehampton | 2023/08/04 09:30 | George Loffhagen v George Houghton | 6-0,6-3 |
| ITF M25 Roehampton | 2023/08/03 09:00 | Toby Samuel v George Loffhagen | 5-7,4-6 |
| ITF M25 Roehampton | 2023/08/02 10:00 | Devin Badenhorst v George Loffhagen | 2-6,7-6,1-6 |
| ITF M25 Roehampton | 2023/08/01 10:35 | Finn Bass v George Loffhagen | 0-6,3-6 |
| Challenger Segovia | 2023/07/25 14:05 | Ricardas Berankis v George Loffhagen | 3-6,6-4,7-6 |
| Wimbledon | 2023/07/04 10:00 | George Loffhagen v Holger Rune | 6-7,3-6,2-6 |
| ATP Eastbourne | 2023/06/26 14:50 | Luca Van Assche v George Loffhagen | 2-6,7-6,7-6 |
| Challenger Nottingham | 2023/06/16 10:00 | Dominik Koepfer v George Loffhagen | 7-5,4-6,6-3 |