Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Limassol | 2023/11/28 08:00 | Jack Karlsson Winstrand v Mihail Ivanov | 6-2,6-2 |
| ITF M15 Limassol | 2023/11/23 11:05 | Jack Karlsson Winstrand v Max Dahlin | 2-6,4-6 |
| ITF M15 Limassol | 2023/11/22 10:00 | Sergis Kyratzis v Jack Karlsson Winstrand | 6-4,4-6,4-6 |
| ITF M15 Limassol | 2023/11/20 10:30 | Jack Karlsson Winstrand v Dean Thurner | 6-0,7-6 |
| ITF M25 Dharwad | 2023/10/16 07:00 | Jack Karlsson Winstrand v Enrico Giacomini | 4-6,6-1,6-10 |
| ITF M25 Dharwad | 2023/10/15 06:30 | Jack Karlsson Winstrand v Dheeraj Kodancha Srinivasan | 6-2,6-3 |
| ITF M15 Ahmedabad | 2023/10/09 04:30 | Jack Karlsson Winstrand v Shivank Bhatnagar | 4-6,7-6,8-10 |
| ITF M15 Ahmedabad | 2023/10/08 04:30 | Jack Karlsson Winstrand v Tarun Karra | 7-5,7-5 |
| 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 |