| ITF M25 Heraklion | 2023/11/29 10:55 | Ioannis Xilas v Neil Oberleitner | 2-6,2-6 |
| ITF M15 Heraklion | 2023/11/25 08:00 | Ioannis Xilas v Alastair Gray | 5-7,0-6 |
| ITF M15 Heraklion | 2023/11/24 12:45 | Benjamin Pietri v Ioannis Xilas | 4-6,1-6 |
| ITF M15 Heraklion | 2023/11/24 08:00 | Ioannis Xilas v Neil Oberleitner | 7-6,6-4 |
| ITF M15 Heraklion | 2023/11/22 10:45 | Ioannis Xilas v Nikolay Nedelchev | 6-2,6-1 |
| UTR Pro Sofia | 2023/09/09 06:30 | Ioannis Xilas v Janos Fekete | 0-1 |
| UTR Pro Sofia | 2023/09/08 06:30 | Ioannis Xilas v Hernando J E Isnardi | 2-6,2-6 |
| UTR Pro Sofia | 2023/09/07 08:00 | Ioannis Xilas v Aniss Rafiq | 6-4,6-2 |
| 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 |
| ITF M25 Heraklion | 2023/11/01 10:10 | Ioannis Kountourakis v Enrico Dalla Valle | 4-6,1-6 |