Stadium: Court 21 Round: 62 Ground: Clay
| ITF - M15 Antalya | 2023/04/17 12:35 | Konstantin Zhzhenov v Simon Freund | 1-6,6-2,10-2 |
| ITF - M15 Antalya | 2023/04/16 07:00 | Maximilian Figl v Simon Freund | 6-1,2-6,5-10 |
| ITF - M15 Monastir | 2023/02/22 12:35 | Simon Freund v Niccolo Baroni | 7-5,4-6,2-6 |
| ITF - M15 Monastir | 2023/02/20 10:25 | Simon Freund v Ruben Hartig | 6-4,6-4 |
| ITF - M15 Monastir | 2023/02/19 09:00 | Simon Freund v Youssef Labbene | 6-1,6-4 |
| ITF - M15 Monastir | 2023/02/15 10:05 | Simon Freund v Ryan Nijboer | 3-6,1-6 |
| 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 | Uladzislau Zhuk v Simon Freund | 1-6,0-6 |
| ITF - M15 Antalya | 2023/04/23 07:00 | Peter Nad v Radovan Michalik | 4-6,5-7 |
| ITF - M15 Antalya | 2023/04/16 07:00 | Radovan Michalik v Maik Steiner | 3-6,6-7 |
| ITF - M15 Antalya | 2023/03/29 12:25 | Radovan Michalik v Sidane Pontjodikromo | 3-6,7-6,3-6 |
| ITF - M15 Antalya | 2023/03/20 11:20 | Elio Jose Ribeiro Lago v Radovan Michalik | 6-3,6-4 |
| ITF - M15 Antalya | 2023/03/19 07:00 | Nika Bidzinashvili v Radovan Michalik | 4-6,1-6 |
| ITF - M15 Antalya | 2023/03/13 16:45 | Jurriaan Bol v Radovan Michalik | 6-4,3-6,10-1 |
| ITF - M15 Antalya | 2023/03/12 12:00 | Radovan Michalik v Carlo Alberto Fossati | 6-3,6-2 |
| ITF - M25 Monastir | 2023/02/19 08:30 | Radovan Michalik v Wei-De Lin | 6-7,6-7 |