Stadium: Court 1 Round: 27 Ground: Hardcourt outdoor
| Challenger Hamburg | 2023/10/15 16:00 | Tristan Lamasine v John Sperle | 2-6,6-2,6-0 |
| ITF M25 Sabadell | 2023/09/28 08:55 | Ryan Nijboer v John Sperle | 6-3,6-1 |
| ITF M25 Sabadell | 2023/09/27 10:15 | John Sperle v Alejandro Juan Mano | 7-5,6-3 |
| ITF M25 Sabadell | 2023/09/26 07:55 | John Sperle v Arthur Bonnaud | 6-4,6-3 |
| ITF M25 Sabadell | 2023/09/25 07:30 | John Sperle v Jiri Cizek | 6-0,6-0 |
| ITF M25 Sabadell | 2023/09/24 07:30 | John Sperle v Carlos Giraldi | 6-0,6-3 |
| ITF M15 Buschhausen | 2023/09/12 10:00 | Justin Engel v John Sperle | 6-2,6-3 |
| ITF M15 Vienna | 2023/09/01 11:25 | Gerald Melzer v John Sperle | 6-2,6-0 |
| ITF M15 Doha | 2023/10/12 13:00 | Marat Sharipov v Olaf Pieczkowski | 6-7,6-2,6-2 |
| ITF M15 Doha | 2023/10/09 15:10 | Mashari Nawaf v Olaf Pieczkowski | 1-6,1-6 |
| ITF M15 Doha | 2023/10/06 12:55 | Coleman Wong v Olaf Pieczkowski | 7-6,6-3 |
| ITF M15 Doha | 2023/10/05 14:20 | Zach Stephens v Olaf Pieczkowski | 3-6,3-6 |
| ITF M15 Doha | 2023/10/04 18:10 | Grigoriy Lomakin v Olaf Pieczkowski | 3-6,4-6 |
| ITF M25 Falun | 2023/09/26 12:00 | Olaf Pieczkowski v Anton Matusevich | 7-6,3-6,4-6 |
| Davis Cup | 2023/09/15 14:35 | Olaf Pieczkowski v Darian King | 1-6,7-6,6-3 |
| ITF M15 Szczawno | 2023/09/03 09:30 | Olaf Pieczkowski v Jasza Szajrych | 6-1,6-2 |