Stadium: Court 6 Round: 26 Ground: Hardcourt outdoor
| ITF M15 - Sharm El Sheikh | 2023/10/04 12:10 | Joshua Sheehy v Stylianos Christodoulou | 6-4,3-6,6-7 |
| ITF M15 - Sharm El Sheikh | 2023/09/30 07:00 | Stuart Parker v Stylianos Christodoulou | 7-6,4-6,6-2 |
| ITF M15 - Sharm El Sheikh | 2023/09/29 07:00 | Stylianos Christodoulou v Tuncay Duran | 6-1,6-3 |
| ITF M15 - Sharm El Sheikh | 2023/09/28 09:40 | Stylianos Christodoulou v Peter Buldorini | 4-6,7-6,6-2 |
| ITF M15 - Sharm El Sheikh | 2023/09/27 10:45 | Zura Tkemaladze v Stylianos Christodoulou | 4-6,5-7 |
| Davis Cup | 2023/06/16 07:30 | Stylianos Christodoulou v Amar Huseinovikj | 6-1,6-2 |
| Davis Cup | 2023/06/15 07:30 | Stylianos Christodoulou v Alex Degabriele | 6-3,6-3 |
| ITF M15 - Alaminos-Larnaca | 2023/05/11 10:05 | Sebastian Gima v Stylianos Christodoulou | 6-2,6-2 |
| ITF M15 - Sharm El Sheikh | 2023/10/04 12:50 | Jacob Bradshaw v Denis Constantin Spiridon | 7-6,6-3 |
| ITF M25 - Darwin | 2023/09/19 08:15 | Jacob Bradshaw v Alexander Klintcharov | 4-6,4-6 |
| ITF M25 - Darwin | 2023/09/15 09:05 | Blake Ellis v Jacob Bradshaw | 6-3,6-2 |
| ITF M25 - Darwin | 2023/09/14 05:30 | Zak Talic v Jacob Bradshaw | 2-6,4-6 |
| ITF M25 - Darwin | 2023/09/12 08:50 | Kody Pearson v Jacob Bradshaw | 6-7,5-7 |
| ITF M15 - Nakhon Si Thammarat | 2023/09/07 02:00 | Jacob Bradshaw v Grigoriy Lomakin | 3-6,7-5,4-6 |
| ITF M15 - Nakhon Si Thammarat | 2023/09/05 03:40 | Jacob Bradshaw v Taiyo Yamanaka | 2-6,6-3,7-6 |
| ITF M15 - Nakhon Si Thammarat | 2023/08/29 02:00 | Leo Vithoontien v Jacob Bradshaw | 6-7,6-3,6-1 |