Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Drummondville | 2023/11/13 15:00 | Olaf Pieczkowski v Alexander Kotzen | 1-6,4-6 |
| Challenger Drummondville | 2023/11/12 16:25 | Olaf Pieczkowski v Marko Stakusic | 7-6,5-7,6-2 |
| ITF M15 Monastir | 2023/11/05 08:30 | Elliot Benchetrit v Olaf Pieczkowski | 6-2,6-3 |
| ITF M15 Monastir | 2023/11/03 08:30 | John Sperle v Olaf Pieczkowski | 3-6,2-6 |
| ITF M15 Monastir | 2023/11/02 10:55 | Fabio De Michele v Olaf Pieczkowski | 4-6,4-6 |
| ITF M15 Monastir | 2023/11/01 08:00 | Diego F Flores v Olaf Pieczkowski | 4-6,6-2,2-6 |
| ITF M15 Monastir | 2023/10/29 08:30 | Olaf Pieczkowski v Alberto Barroso Campos | 1-6,1-6 |
| ITF M15 Monastir | 2023/10/28 08:30 | Guido Ivan Justo v Olaf Pieczkowski | 6-1,6-7,3-6 |
| Challenger Calgary | 2023/11/08 04:30 | Gabriel Diallo v Andrew Paulson | 4-6,7-6,6-4 |
| Challenger Ismaning | 2023/11/03 12:40 | Andrew Paulson v Maximilian Marterer | 2-6,4-6 |
| Challenger Ismaning | 2023/11/01 10:00 | Timo Stodder v Andrew Paulson | 6-7,3-6 |
| Challenger Ismaning | 2023/10/31 10:00 | Andrew Paulson v Louis Wessels | 6-4,6-7,6-3 |
| Challenger Ismaning | 2023/10/30 14:15 | Andrew Paulson v Tom Gentzsch | 3-6,7-6,7-6 |
| Challenger Ismaning | 2023/10/29 15:50 | Andrew Paulson v Jakob Schnaitter | 6-3,7-5 |
| Challenger Ortisei | 2023/10/24 10:25 | Andrew Paulson v Lukáš Klein | 5-7,4-6 |
| Challenger Hamburk | 2023/10/15 13:10 | Andrew Paulson v Daniel Masur | 3-6,2-6 |