| ITF M15 - Heraklion | 03/19 07:00 | 62 | Miko Wassermann v Stylianos Christodoulou | 1-6,1-6 | |
| ITF M25 - Heraklion | 03/12 07:00 | 62 | Linus Videhult v Stylianos Christodoulou | 3-6,7-6,10-8 | |
| ITF M25 - Heraklion | 11/22 11:45 | 25 | Stylianos Christodoulou v Filip Peliwo | 6-3,2-6,5-7 | |
| ITF M25 - Heraklion | 11/15 10:35 | 25 | Daniel Cukierman v Stylianos Christodoulou | 6-0,6-4 | |
| ITF M15 - Heraklion | 11/08 07:30 | 62 | Dax Donders v Stylianos Christodoulou | 7-5,6-4 | |
| ITF M15 - Heraklion | 11/06 09:30 | 62 | Yair Sarouk v Stylianos Christodoulou | 1-6,2-6 | |
| ITF M15 - Heraklion | 10/23 08:30 | 44 | Christos Antonopoulos v Stylianos Christodoulou | 5-7,6-4,10-6 | |
| ITF M15 - Heraklion | 10/16 12:00 | 44 | Raz Haviv v Stylianos Christodoulou | 6-0,6-2 | |
| ITF M15 - Heraklion | 10/15 06:30 | 28 | Stylianos Christodoulou v David Pichler | 1-6,0-6 | |
| ITF M15 - Heraklion | 10/14 07:00 | 27 | Stylianos Christodoulou v Ben Weintraub | 6-4,6-2 | |
| ITF M15 - Heraklion | 10/13 10:50 | 26 | Andrea Guerrieri v Stylianos Christodoulou | 3-6,6-3,5-7 | |
| ITF M15 - Heraklion | 10/11 08:00 | 25 | Stylianos Christodoulou v Stephanos Schinas | 6-1,6-1 | |
| Davis Cup | 03/05 13:05 | 45 | Amr Asrawy v Stylianos Christodoulou | 6-3,6-3 | |
| ITF M25 - Sharm El Sheikh | 02/06 07:30 | 62 | Illya Beloborodko v Stylianos Christodoulou | 6-4,6-3 | |
| ITF M25 - Sharm El Sheikh | 02/01 09:15 | 62 | Sahar Simon v Stylianos Christodoulou | 6-3,6-7,15-13 | |
| ITF M25 - Sharm El Sheikh | 01/31 13:20 | 62 | Gillian Osmont v Stylianos Christodoulou | 1-6,1-6 | |
| ITF M15 - Heraklion | 12/03 09:40 | 27 | Stylianos Christodoulou v Arthur Fery | Walkover | |
| ITF M15 - Heraklion | 12/02 10:00 | 26 | Aristotelis Thanos v Stylianos Christodoulou | Retired | |
| ITF M15 - Heraklion | 12/01 10:40 | 25 | Filip Kana v Stylianos Christodoulou | 1-6,2-6 | |
| ITF M15 - Heraklion | 11/30 07:00 | 62 | Stylianos Christodoulou v Radu F Macovei | 6-2,6-3 | |
| ITF M15 - Heraklion | 11/29 09:00 | 62 | Stylianos Christodoulou v Maxim Khorozov | 6-1,7-5 | |
| ITF M15 - Sharm El Sheikh | 10/28 10:05 | 26 | Hady Habib v Stylianos Christodoulou | 6-2,6-2 | |
| ITF M15 - Sharm El Sheikh | 10/27 10:50 | 25 | Stylianos Christodoulou v Faris Zakaryia | 4-6,6-4,6-3 | |
| ITF M15 - Sharm El Sheikh | 10/26 09:10 | 62 | Stylianos Christodoulou v Roy Hobbs | 6-3,6-1 | |
| ITF M15 - Sharm El Sheikh | 10/25 08:00 | 62 | Stylianos Christodoulou v Matias Riva | 6-3,6-3 | |
| ITF M15 - Sharm El Sheikh | 10/24 09:30 | 62 | Laelson Rodrigues v Stylianos Christodoulou | 3-6,3-6 | |
| ITF M15 - Doha | 10/12 12:30 | 44 | Boris Butulija v Stylianos Christodoulou | 6-1,7-6 | |
| ITF M15 - Doha | 10/11 13:30 | 44 | Stylianos Christodoulou v Daniil Savelev | Retired | |
| ITF M15 - Doha - Kvalifikation | 10/10 12:55 | 44 | Sultan K. Al Alawi v Stylianos Christodoulou | 6-3,5-7,1-10 |