Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF M25 - Heraklion | 2023/11/01 10:10 | Ioannis Kountourakis v Enrico Dalla Valle | 4-6,1-6 |
| ITF M15 - Heraklion | 2023/10/25 06:30 | Guy Den Ouden v Ioannis Kountourakis | 7-5,6-4 |
| ITF M25 - Heraklion | 2023/11/28 07:30 | Raphael Calzi v Max Benaim | 3-6,2-6 |
| ITF M25 - Heraklion | 2023/11/27 11:30 | Lars Goran Verwerft v Max Benaim | 5-7,3-6 |
| ITF M15 - Heraklion | 2023/11/20 10:00 | Jannik Maute v Max Benaim | 6-4,6-2 |
| ITF M25 - Heraklion | 2023/11/13 08:30 | Benjamin Pietri v Max Benaim | 6-4,7-5 |
| ITF M25 - Heraklion | 2023/11/12 07:00 | Max Benaim v Maximo Nagele | 6-1,6-1 |
| ITF M25 - Glasgow | 2023/10/22 14:45 | Charlie Robertson v Max Benaim | 6-3,6-2 |
| ITF M25 - Monastir | 2023/09/11 13:45 | Max Benaim v Felix Mischker | 2-6,3-6 |
| ITF M25 - Monastir | 2023/09/11 09:50 | Max Benaim v Filippo Giovannini | 6-3,7-6 |