| 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 Heraklion | 2023/11/21 07:00 | Ioannis Kountourakis v Rodrigo Alujas | 6-4,3-6,5-10 |
| ITF M15 Heraklion | 2023/11/20 10:00 | Ioannis Kountourakis v Arthur Van Der Kooij | 7-6,6-3 |
| ITF M25 Heraklion | 2023/11/13 13:45 | Ioannis Kountourakis v Noah Merre | 6-7,1-6 |
| ITF M25 Heraklion | 2023/11/12 13:00 | Ioannis Kountourakis v Tom Varzandeh | 6-3,6-3 |
| ITF M25 Heraklion | 2023/11/07 10:15 | Daniele Rapagnetta v Ioannis Kountourakis | 6-4,7-5 |
| ITF M25 Heraklion | 2023/11/05 11:00 | Kevin Edengren v Ioannis Kountourakis | 2-6,6-7 |
| UTR Pro Olomouc | 2023/11/12 07:00 | David Schwarc v Rafael Kis Balazs | 1-1 |
| UTR Pro Olomouc | 2023/11/11 10:00 | Christos Keisidis v David Schwarc | 2-6,4-6 |
| UTR Pro Olomouc | 2023/11/10 11:17 | David Schwarc v Robert Rumler | 6-4,6-4 |
| UTR Pro Olomouc | 2023/11/08 11:30 | David Schwarc v Domagoj Biljesko | 4-6,1-5 |
| UTR Pro Olomouc | 2023/11/07 11:30 | David Schwarc v Karol Filar | 3-6,5-7 |
| UTR Pro Olomouc | 2023/11/06 10:39 | Jan Kusy v David Schwarc | 6-1,6-1 |