Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Monastir | 2023/02/13 12:45 | Jasza Szajrych v Simon Freund | 1-6,1-6 |
| ITF - M15 Monastir | 2023/02/12 13:30 | Zhuk, Uladzislau v Simon Freund | 1-6,0-6 |
| ITF - M15 Monastir | 2023/02/08 10:45 | Fabrizio Andaloro v Simon Freund | 6-0,6-3 |
| ITF - M15 Monastir | 2023/02/06 10:20 | Vito Tonejc v Simon Freund | 4-6,6-1,8-10 |
| ITF - M15 Monastir | 2023/02/05 11:00 | Kirill Mishkin v Simon Freund | 2-6,3-6 |
| ITF - M25 Sunderland | 2023/01/23 10:00 | Simon Freund v James Davis | 2-6,3-6 |
| ITF - M25 Sunderland | 2023/01/22 12:00 | Simon Freund v Onuma, Yujiro | 7-6,6-4 |
| ITF M25 Sheffield | 2023/01/17 13:25 | Harry Wendelken v Simon Freund | 7-5,6-2 |
| ITF - M15 Monastir | 2023/02/12 08:30 | Ryan Nijboer v Olaf Pieczkowski | 7-6,6-2 |
| ITF - M15 Monastir | 2023/02/11 14:30 | Ryan Nijboer v Nicolas Tepmahc | 6-2,6-2 |
| ITF - M15 Monastir | 2023/02/11 10:45 | Ryan Nijboer v Florent Bax | 7-5,6-2 |
| ITF - M15 Monastir | 2023/02/09 09:30 | Kris Van Wyk v Ryan Nijboer | 6-7,6-2,4-6 |
| ITF - M15 Monastir | 2023/02/01 10:45 | Ryan Nijboer v Perez Sanz, David | 6-7,7-5,3-6 |
| ITF M15 Madrid | 2022/12/09 11:20 | Miguel Damas v Ryan Nijboer | 3-6,6-2,6-0 |
| ITF M15 Madrid | 2022/12/08 10:00 | Ryan Nijboer v Alejandro Moro Canas | 1-6,6-3,6-4 |
| ITF M15 Madrid | 2022/12/06 11:00 | Diego F Flores v Ryan Nijboer | 1-6,4-6 |