Stadium: Court 3 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Monastir | 2023/02/07 12:00 | Dan Added v Ilia Simakin | 6-4,6-2 |
| ITF M25 Monastir | 2023/01/31 10:40 | Benjamin Pietri v Ilia Simakin | 6-4,6-2 |
| ITF M15 Monastir | 2023/01/26 11:30 | Francesco Forti v Ilia Simakin | 6-3,6-4 |
| ITF M15 Monastir | 2023/01/24 10:20 | Simon A Ivanov v Ilia Simakin | 2-6,0-6 |
| ITF M15 Sharm El Sheikh | 2022/12/07 13:35 | Ilia Simakin v Kris Van Wyk | 5-7,5-7 |
| ITF M15 Sharm El Sheikh | 2022/12/02 08:00 | Lukas Krainer v Ilia Simakin | 7-6,6-3 |
| ITF M15 Sharm El Sheikh | 2022/12/01 08:00 | Ilia Simakin v Saba Purtseladze | 6-4,6-4 |
| ITF M15 Sharm El Sheikh | 2022/11/30 11:10 | Nicolo Pozzani v Ilia Simakin | 1-6,6-7 |
| ITF M15 Sharm El Sheikh | 2023/02/05 14:00 | George Gregoriou v Dinko Dinev | 2-6,2-6 |
| ITF M15 Sharm El Sheikh | 2022/12/05 08:00 | Freddie Ridout v George Gregoriou | 2-6,7-5,11-9 |
| ITF M15 Sharm El Sheikh | 2022/12/04 08:00 | Myroslav Bondar v George Gregoriou | 6-4,2-6,6-10 |
| ITF M15 Sharm El Sheikh | 2022/11/28 08:00 | Alessio Savoldi v George Gregoriou | 6-2,6-3 |
| ITF M15 Sharm El Sheikh | 2022/11/20 10:30 | Anthony Wright v George Gregoriou | 6-4,6-0 |
| ITF M25 Monastir | 2022/10/23 10:30 | George Gregoriou v Stevan Popovic | 1-6,2-6 |
| ITF M15 Monastir | 2022/10/16 08:00 | George Gregoriou v Niklas Rohrer | 0-6,2-6 |
| ITF M15 Monastir | 2022/10/09 08:00 | George Gregoriou v Wei-De Lin | 2-6,1-6 |