Stadium: Court 5 Round: 25 Ground: Clay
| ITF M25 - Pazardzhik | 2023/09/25 10:00 | Nikola Kolyachev v Martin Dimitrov | 6-4,6-2 |
| ITF M25 - Pazardzhik | 2023/09/25 07:00 | Nikola Kolyachev v Vladimir Kravec | 6-0,6-1 |
| ITF M15 - Pirot | 2023/09/05 07:25 | Alexander Chepik v Nikola Kolyachev | 6-4,2-6,10-8 |
| ITF M15 - Pirot | 2023/09/04 08:30 | Nikola Mitrovic v Nikola Kolyachev | 3-6,0-6 |
| ITF M15 - Targu Jiu | 2023/08/15 10:40 | Radovan Michalik v Nikola Kolyachev | 6-2,4-6,11-9 |
| ITF M15 - Targu Jiu | 2023/08/13 06:30 | Nikola Kolyachev v Gheorghe Claudiu Schinteie | 6-1,7-6 |
| ITF M15 - Curtea de Arges | 2023/08/10 08:00 | Nikola Kolyachev v Luciano Emanuel Ambrogi | 1-6,4-6 |
| ITF M15 - Curtea de Arges | 2023/08/09 07:00 | Nikola Kolyachev v Elio Jose Ribeiro Lago | 6-4,6-1 |
| ITF M25 - Pazardzhik | 2023/09/25 13:55 | Maxwell Benson v Felipe Mikkelsen | 7-6,6-4 |
| ITF M25 - Pazardzhik | 2023/09/25 07:00 | Vojtech Vlkovsky v Maxwell Benson | 3-6,0-6 |
| ITF M25 - Pardubice | 2023/09/18 10:30 | Tom Schonenberg v Maxwell Benson | 6-1,6-2 |
| ITF M25 - Pardubice | 2023/09/17 12:00 | Josef Vagner v Maxwell Benson | 4-6,2-6 |
| ITF M15 - Satu Mare | 2023/09/12 07:00 | Juan Cruz Martin Manzano v Maxwell Benson | 7-6,6-3 |
| ITF M15 - Satu Mare | 2023/09/11 07:00 | Botond Kisantal v Maxwell Benson | 4-6,0-6 |
| ITF M15 - Satu Mare | 2023/09/10 07:00 | Maxwell Benson v Ioan A Teglas | 6-3,6-3 |
| ITF M25 - Jablonec Nad Nisou | 2023/08/27 08:00 | Vitek Horak v Maxwell Benson | 6-3,7-5 |