Stadium: Court 5 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Sharm El Sheikh | 2022/12/05 08:00 | Freddie Ridout v George Gregoriou | 2-6,7-5,11-9 |
| ITF M25 Sharm El Sheikh | 2023/09/18 08:20 | Karim El Feky v George Gregoriou | 6-1,7-6 |
| ITF M25 Monastir | 2023/09/10 08:00 | Alvaro Dagoberto Garcia Ramirez v George Gregoriou | 6-3,6-3 |
| ITF M25 Monastir | 2023/09/04 14:00 | Mohammad Alkotop v George Gregoriou | 6-2,7-5 |
| ITF M25 Monastir | 2023/09/04 08:00 | George Gregoriou v Alexey Dubinin | 3-6,6-3,10-2 |
| ITF M15 Monastir | 2023/08/28 08:00 | George Gregoriou v Ammar Faleh Alhogbani | 1-6,1-6 |
| ITF M15 Monastir | 2023/08/14 08:00 | Stefan Vujic v George Gregoriou | 6-2,6-1 |
| ITF M15 Monastir | 2023/08/07 08:00 | Michal Krajci v George Gregoriou | 6-3,6-2 |
| ITF M15 Monastir | 2023/07/30 07:30 | George Gregoriou v Patrick Kotan | 3-6,3-6 |
| ITF M25 Sharm El Sheikh | 2023/09/20 13:40 | Tuncay Duran v Freddie Ridout | 3-6,6-3,6-3 |
| ITF M25 Aldershot | 2023/08/13 11:15 | Freddie Ridout v Damien Salvestre | 1-6,3-6 |
| ITF M25 Roehampton | 2023/08/06 13:00 | Freddie Ridout v Ali Habib | 3-6,2-6 |
| ITF M25 Roehampton | 2023/07/30 09:00 | Freddie Ridout v Ali Habib | 1-6,2-6 |
| ITF M25 Nottingham | 2023/07/09 11:35 | Freddie Ridout v Billy Blaydes | 3-6,2-6 |
| ITF M25 Nottingham Qual | 2023/04/24 11:50 | Freddie Ridout v George Houghton | 2-6,2-6 |
| ITF M15 Sharm El Sheikh | 2023/04/03 08:30 | Freddie Ridout v Aleksandr Lobanov | 0-6,1-6 |
| ITF M15 Sharm El Sheikh | 2023/04/02 10:00 | Freddie Ridout v Pavlo Rezoglazov | 6-0,6-2 |