Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Limassol | 2023/11/25 08:00 | Jakub Nicod v Olaf Pieczkowski | 6-2,5-7,6-2 |
| ITF M15 Limassol | 2023/11/24 10:00 | Sebastian Sorger v Olaf Pieczkowski | 6-4,2-6,3-6 |
| ITF M15 Limassol | 2023/11/23 09:25 | Kevin Edengren v Olaf Pieczkowski | 3-6,1-6 |
| ITF M15 Limassol | 2023/11/22 13:15 | Christopher Papa v Olaf Pieczkowski | 6-7,0-6 |
| Challenger Drummondville | 2023/11/16 23:30 | Dominik Koepfer v Olaf Pieczkowski | 6-4,6-4 |
| Challenger Drummondville | 2023/11/14 15:00 | Olaf Pieczkowski v Andrew Paulson | 4-6,6-3,6-1 |
| 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 |
| UTR Pro Easton | 2023/11/18 09:30 | Alex Levine Zuckerman v Freddie Ridout | 6-3,6-4 |
| UTR Pro Easton | 2023/11/17 12:30 | Freddie Ridout v Ewen Lumsden | 3-6,1-6 |
| UTR Pro Easton | 2023/11/16 10:33 | Freddie Ridout v Ed Pudney | 2-6,2-5 |
| UTR Pro Easton | 2023/11/15 08:00 | Brody Nejedly-Krall v Freddie Ridout | 2-6,6-4,3-6 |
| UTR Pro Easton | 2023/11/14 13:23 | Hugo Coquelin v Freddie Ridout | 6-0,6-0 |
| ITF M15 Sharm El Sheikh | 2023/10/08 11:00 | Tom Varzandeh v Freddie Ridout | 6-2,7-5 |
| ITF M15 Sharm El Sheikh | 2023/10/02 07:00 | Sean Van Rensburg v Freddie Ridout | 6-2,6-4 |
| ITF M15 Sharm El Sheikh | 2023/09/27 10:10 | Freddie Ridout v David Quayle | 4-6,3-6 |