Stadium: Court 6 Round: 54 Ground: Carpet indoor
| ITF M15 Cadolzburg | 2024/01/14 11:30 | Ioannis Kountourakis v Tobias Brutscher | 6-4,6-1 |
| UTR Pro Athens | 2023/12/17 10:45 | Christos Keisidis v Ioannis Kountourakis | 6-3,6-6 |
| UTR Pro Athens | 2023/12/15 07:30 | Ioannis Kountourakis v Illya Beloborodko | 6-2,6-3 |
| UTR Pro Athens | 2023/12/13 06:00 | Ioannis Kountourakis v Lefteris Neos | 6-1,4-6,6-4 |
| UTR Pro Athens | 2023/12/12 09:17 | Ioannis Kountourakis v David Schwarc | 6-2,6-2 |
| UTR Pro Athens | 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 |
| ITF M15 Heráklion | 2023/11/21 07:00 | Ioannis Kountourakis v Rodrigo Alujas | 6-4,3-6,5-10 |
| ITF M15 Cadolzburg | 2024/01/14 11:30 | Mihailo Milenkovic v Henrik Bladelius | 6-3,6-7,10-7 |
| ITF M15 Monastir | 2024/01/07 12:00 | Mihailo Milenkovic v Oscar Moraing | 2-6,1-6 |
| ITF M15 Monastir | 2024/01/01 09:00 | Alexander Brown v Mihailo Milenkovic | 6-4,6-3 |
| ITF M15 Monastir | 2023/10/23 08:00 | Mihailo Milenkovic v Filippo Mazzola | 1-6,1-6 |
| ITF M15 Monastir | 2023/10/22 08:00 | Davide Galvanin v Mihailo Milenkovic | 6-4,4-6,9-11 |
| ITF M15 Frankfurt Nad Mohanem | 2023/08/08 15:30 | Mihailo Milenkovic v Andrey Chepelev | 6-3,2-6,3-6 |