Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Ismaning | 2023/11/01 11:55 | Henri Squire v Marc-Andrea Huesler | 3-6,7-5,6-7 |
| Challenger Ismaning | 2023/10/30 16:35 | Denis Yevseyev v Henri Squire | 3-6,4-6 |
| Challenger Lisbon | 2023/10/02 09:00 | Henri Squire v Francesco Forti | 7-6,1-6,1-6 |
| Challenger Lisbon | 2023/10/01 09:00 | Henri Squire v Connor Thomson | 6-4,3-6,6-1 |
| Challenger Braga | 2023/09/24 12:15 | Henri Squire v Tiago Pereira | 3-6,6-3,1-6 |
| Challenger Bad Waltersdorf | 2023/09/19 13:10 | Raul Brancaccio v Henri Squire | 7-6,5-7,6-2 |
| Challenger Bad Waltersdorf | 2023/09/18 08:00 | Henri Squire v Marcello Serafini | 6-4,6-2 |
| Challenger Bad Waltersdorf | 2023/09/17 08:00 | Henri Squire v David Pichler | 6-7,6-3,6-4 |
| ITF M15 Al Zahra | 2023/11/01 07:00 | Peter Benjamin Privara v Tomas Lanik | 3-6,4-6 |
| ITF M15 Al Zahra | 2023/10/27 08:00 | Peter Benjamin Privara v Aleksandre Bakshi | 5-7,6-7 |
| ITF M15 Al Zahra | 2023/10/26 08:25 | Peter Benjamin Privara v Volodymyr Iakubenko | 7-6,6-2 |
| ITF M15 Al Zahra | 2023/10/24 12:30 | Peter Benjamin Privara v Aljaz Jeran | 6-3,6-0 |
| ITF M15 Monastir | 2023/10/07 08:30 | Kai Wehnelt v Peter Benjamin Privara | 4-6,6-2,6-2 |
| ITF M15 Monastir | 2023/10/06 10:00 | Peter Benjamin Privara v Roberto Cid Subervi | 7-5,6-2 |
| ITF M15 Monastir | 2023/10/05 09:50 | Peter Benjamin Privara v Carlo A Caniato | 6-4,6-4 |
| ITF M15 Monastir | 2023/10/04 08:30 | Peter Benjamin Privara v Isaac Nortey | 7-5,6-1 |