Stadium: Court 7 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/12/26 12:30 | Simakin, Ilia v Chirag Duhan | 6-1,7-6 |
| ITF M25 Sharm El Sheikh | 2023/11/08 08:00 | Simakin, Ilia v Bor Artnak | 6-7,3-6 |
| ITF M25 Sharm El Sheikh | 2023/11/02 09:35 | Simakin, Ilia v van Wyk, Kris | 7-6,3-6,2-6 |
| ITF M25 Sharm El Sheikh | 2023/11/01 13:45 | 리우, 한이 v Simakin, Ilia | 3-6,4-6 |
| ITF M15 Sharm El Sheikh | 2023/10/27 08:00 | Simakin, Ilia v 푸르트셀라드즈, 사바 | 4-6,6-4,4-6 |
| ITF M15 Sharm El Sheikh | 2023/10/26 07:00 | Simakin, Ilia v 우르수, 바딤 | 6-3,6-2 |
| ITF M15 Sharm El Sheikh | 2023/10/25 08:10 | Simakin, Ilia v Salton, Dylan | 6-1,6-1 |
| ITF M15 Sharm El Sheikh | 2023/10/18 11:25 | 빈다, 알렉산들 v Simakin, Ilia | 7-6,1-6,6-2 |
| ITF M15 Monastir | 2023/12/27 17:40 | Gregg, Perry v 마클로프, 모하메드 나짐 | 6-4,7-6 |
| ITF M15 Monastir | 2023/12/23 08:30 | Mariano Tammaro v Gregg, Perry | 6-3,6-3 |
| ITF M15 Monastir | 2023/12/22 11:05 | Tomasz Berkieta v Gregg, Perry | 3-6,6-4,1-6 |
| ITF M15 Monastir | 2023/12/21 10:30 | Ignasi Forcano v Gregg, Perry | 3-6,2-6 |
| ITF M15 Monastir | 2023/12/20 12:30 | Gregg, Perry v Bertimon, Charles | 5-7,7-6,8-10 |
| ITF M15 Monastir | 2023/12/20 08:15 | Gregg, Perry v Matteo Fondriest | 6-1,6-1 |
| ITF M15 Monastir | 2023/12/18 12:15 | Gregg, Perry v 반 누넨, 맥스 | 6-1,6-3 |
| ITF M15 East Lansing | 2023/11/17 17:20 | Gregg, Perry v Colak, Ozan | 2-6,4-6 |