Stadium: Court 5 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 M15 Sharm El Sheikh | 2023/12/03 08:00 | Sergo Sikharulidze v Jabari Stafford | 6-2,6-2 |
| ITF M15 Heraklion | 2023/11/20 07:00 | Sergo Sikharulidze v Thomas Kostka | 0-6,0-6 |
| ITF M25 Heraklion | 2023/11/13 13:45 | Jannik Maute v Sergo Sikharulidze | 6-2,6-1 |
| ITF M25 Heraklion | 2023/11/12 12:00 | Nicola Ion v Sergo Sikharulidze | 7-5,0-6,8-10 |
| ITF M25 Telavi | 2023/10/24 06:00 | Jeremy Gschwendtner v Sergo Sikharulidze | 6-0,6-3 |
| ITF M25 Telavi | 2023/10/23 06:00 | Heng Yi Zhang v Sergo Sikharulidze | 3-6,0-6 |
| ITF M25 Telavi | 2023/10/15 08:30 | Josh Reid v Sergo Sikharulidze | 6-4,6-3 |
| ITF M25 Telavi | 2023/10/10 06:00 | Sergo Sikharulidze v Maxence Bertimon | 1-6,3-6 |