Estádio: Court 5 Round: 25 Ground: Carpet indoor
| Campeonato da Alemanha | 2023/12/07 14:35 | Leopold Zima v Jakob Schnaitter | 3-6,4-6 |
| Campeonato da Alemanha | 2023/12/06 14:10 | Leopold Zima v Markus Malaszszak | 6-1,6-1 |
| Challenger - Maia | 2023/11/26 11:00 | Miguel Damas v Leopold Zima | 6-3,6-4 |
| ITF - M25 Vale do Lobo | 2023/11/24 12:45 | Henrique Rocha v Leopold Zima | 6-2,7-5 |
| ITF - M25 Vale do Lobo | 2023/11/23 12:00 | Leopold Zima v Alexey Vatutin | 6-3,4-6,6-4 |
| ITF - M25 Vale do Lobo | 2023/11/22 10:00 | Pietro Pampanin v Leopold Zima | 3-6,5-7 |
| ITF - M25 Vale do Lobo | 2023/11/13 11:00 | Leopold Zima v Tiago Boschmans | 4-6,6-1,10-12 |
| ITF - M25 Trnava | 2023/11/06 14:00 | Aleksander Chayka v Leopold Zima | 2-6,7-6,10-5 |
| ITF - M15 Cadolzburg | 2024/01/15 10:00 | Ioannis Kountourakis v Mihailo Milenkovic | 6-4,6-1 |
| ITF - M15 Cadolzburg | 2024/01/14 11:30 | Ioannis Kountourakis v Tobias Brutscher | 6-4,6-1 |
| UTR Pro - Atenas | 2023/12/17 10:45 | Christos Keisidis v Ioannis Kountourakis | 6-3,6-6 |
| UTR Pro - Atenas | 2023/12/15 07:30 | Ioannis Kountourakis v Illya Beloborodko | 6-2,6-3 |
| UTR Pro - Atenas | 2023/12/13 06:00 | Ioannis Kountourakis v Lefteris Neos | 6-1,4-6,6-4 |
| UTR Pro - Atenas | 2023/12/12 09:17 | Ioannis Kountourakis v David Schwarc | 6-2,6-2 |
| UTR Pro - Atenas | 2023/12/11 10:10 | Ioannis Xilas v Ioannis Kountourakis | 6-4,6-0 |
| ITF - M25 Heraklion | 2023/11/29 09:15 | Ioannis Kountourakis v Max Benaim | 5-7,3-6 |