Stadium: Court 7 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Sharm El Sheikh | 2023/11/27 08:00 | Aleksander Chayka v Andrea Fiorentini | 2-6,3-6 |
| ITF M25 Trnava | 2023/11/09 11:35 | Aleksander Chayka v Tibo Colson | 4-6,4-6 |
| ITF M25 Trnava | 2023/11/08 16:25 | Elmar Ejupovic v Aleksander Chayka | 7-6,4-6,6-7 |
| ITF M25 Trnava | 2023/11/07 12:15 | Michael Gloeckler v Aleksander Chayka | 3-6,7-6,7-10 |
| ITF M25 Trnava | 2023/11/06 14:00 | Aleksander Chayka v Leopold Zima | 2-6,7-6,10-5 |
| ITF M25 Sharm El Sheikh | 2023/10/30 10:20 | Yuquan Jin v Aleksander Chayka | 6-3,6-4 |
| ITF M15 Sharm El Sheikh | 2023/10/24 07:00 | Aleksander Chayka v Jakub Kroslak | 3-6,2-6 |
| ITF M15 Sharm El Sheikh | 2023/10/23 07:00 | Aleksander Chayka v Andriy Poritskyy | 7-5,6-4 |
| ITF M25 Heraklion | 2023/11/05 11:00 | Gianluca Carlini v Yan Sabanin | 4-6,3-6 |
| ITF M25 Heraklion | 2023/10/29 10:30 | Gianluca Carlini v Gabriel Matuszewski | 6-7,1-6 |
| ITF M15 Heraklion | 2023/10/23 09:00 | Jonas Trinker v Gianluca Carlini | 6-3,6-4 |
| ITF M15 Heraklion | 2023/10/22 08:30 | Oskar Grzegorzewski v Gianluca Carlini | 4-6,4-6 |
| ITF M15 Heraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| ITF M15 Monastir | 2023/09/25 12:30 | Ludovico Vaccari v Gianluca Carlini | 6-4,6-4 |
| ITF M15 Monastir | 2023/09/25 08:30 | Samyar Elyasi v Gianluca Carlini | 0-6,1-6 |
| ITF M15 Monastir | 2023/09/24 08:30 | Gianluca Carlini v Enmanuel Munoz | 3-6,6-3,10-3 |