Stadium: Court 5 Round: 44 Ground: Clay
| ITF M25 Pazardzhik | 2023/10/01 10:00 | Artsiom Sinitsyn v Anthony Shumsky | 1-6,6-2,6-10 |
| ITF M25 Pazardzhik | 2023/09/24 07:00 | Mal Agushi v Anthony Shumsky | 1-6,7-5,10-7 |
| ITF M15 Kursumlijska Banja | 2023/09/17 14:30 | Yuquan Jin v Anthony Shumsky | 6-1,6-1 |
| ITF M25 Yinchuan | 2023/08/13 02:00 | Anthony Shumsky v Shenglin Zhuo | 2-6,3-6 |
| ITF M25 Baotou | 2023/08/07 01:25 | Anthony Shumsky v Yanjie Zheng | 6-1,4-6,4-10 |
| ITF M25 Baotou | 2023/08/06 03:25 | Anthony Shumsky v Min Seong Kim | 5-7,6-4,10-5 |
| ITF M25 Anning | 2023/07/30 01:00 | Anthony Shumsky v Xiaochuan Tang | 4-6,0-6 |
| ITF M15 Monastir | 2023/05/24 12:30 | Anthony Shumsky v Calum Puttergill | 0-6,2-6 |
| ITF M25 Pazardzhik | 2023/09/27 12:35 | Nikola Kolyachev v Maxwell Benson | 6-4,7-6 |
| 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 |