Estádio: Match Court Round: 2
| ITF - M15 Szczawno-Zdrój | 2023/09/03 09:30 | Olaf Pieczkowski v Jasza Szajrych | 6-1,6-2 |
| ITF - M15 Szczawno-Zdrój | 2023/09/01 09:00 | Olaf Pieczkowski v Jonas P Hartenstein | 6-2,6-2 |
| ITF - M15 Szczawno-Zdrój | 2023/08/30 07:00 | Olaf Pieczkowski v Alan Bojarski | 6-0,6-2 |
| ITF - M25 Poznan | 2023/08/23 13:45 | Olaf Pieczkowski v Viacheslav Bielinskyi | 6-3,3-6,2-6 |
| ITF - M25 Bielsko-Biała | 2023/08/18 08:30 | Juan Bautista Torres v Olaf Pieczkowski | 6-3,6-2 |
| ITF - M25 Bielsko-Biała | 2023/08/17 08:30 | Olaf Pieczkowski v Daniel Siniakov | 7-5,6-2 |
| ITF - M25 Bielsko-Biała | 2023/08/16 09:00 | Ondrej Horak v Olaf Pieczkowski | 6-3,1-6,0-6 |
| ITF - M25 Łódź | 2023/08/10 10:30 | Daniel Paty v Olaf Pieczkowski | 6-3,6-2 |
| ATP - Winston-Salem | 2023/08/21 22:15 | Michael Mmoh v Darian King | 6-2,3-6,6-3 |
| ATP - Winston-Salem | 2023/08/20 17:00 | Strong Kirchheimer v Darian King | 6-2,4-6,6-7 |
| ATP - Winston-Salem | 2023/08/19 16:35 | Darian King v Ulises Blanch | 2-6,6-4,6-3 |
| Challenger - Winnipeg | 2023/08/17 18:45 | Darian King v Ryan Peniston | 0-6,1-6 |
| Challenger - Winnipeg | 2023/08/16 17:00 | Benjamin Bonzi v Darian King | 3-6,1-6 |
| Challenger - Winnipeg | 2023/08/15 16:00 | Darian King v Brayden Schnur | 6-2,6-1 |
| Challenger - Winnipeg | 2023/08/14 18:50 | Matija Pecotic v Darian King | 3-6,4-6 |
| Challenger - Winnipeg | 2023/08/13 22:05 | Joshua Sheehy v Darian King | 6-3,1-6,3-6 |