| ITF M15 - Heraklion | 05/29 09:00 | 62 | Ioannis Kountourakis v Tom Evans | 7-5,2-6,5-10 | |
| ITF M15 - Heraklion | 05/25 08:30 | 25 | Ioannis Kountourakis v Mark Whitehouse | 3-6,3-6 | |
| ITF M15 - Heraklion | 05/24 07:00 | 62 | Kai Lemstra v Ioannis Kountourakis | 6-7,5-7 | |
| ITF M15 - Heraklion | 05/23 08:30 | 62 | Dorian Kos v Ioannis Kountourakis | 3-6,2-6 | |
| ITF M15 - Heraklion | 05/18 07:00 | 25 | Mark Lajal v Ioannis Kountourakis | 7-6,6-4 | |
| ITF M15 - Heraklion | 05/10 08:30 | 25 | Aaron Addison v Ioannis Kountourakis | 6-3,6-1 | |
| ITF M15 - Sharm El Sheikh | 02/13 08:30 | 62 | Aaron Cohen v Ioannis Kountourakis | 1-6,7-5,10-6 | |
| ITF M25 - Sharm El Sheikh | 02/07 09:20 | 62 | Lior Goldenberg v Ioannis Kountourakis | 7-6,7-6 | |
| ITF M25 - Sharm El Sheikh | 01/31 08:00 | 62 | Ioannis Kountourakis v Juan Manuel Benitez Chavarriaga | 3-6,6-7 | |
| ITF M25 - Sharm El Sheikh | 01/30 08:00 | 62 | Yan Brek v Ioannis Kountourakis | 1-6,2-6 | |
| ITF M25 - Cairo | 01/25 08:00 | 62 | Ray Ho v Ioannis Kountourakis | 7-5,6-0 | |
| ITF M25 - Cairo | 01/24 08:00 | 62 | Ioannis Kountourakis v Faris Zakaryia | 7-6,3-6,10-6 | |
| ITF M25 - Cairo | 01/23 08:30 | 62 | Gunjan Jadhav v Ioannis Kountourakis | 3-6,2-6 | |
| ITF M15 - Heraklion | 11/30 07:00 | 62 | Roi Ginat v Ioannis Kountourakis | 7-5,6-3 | |
| ITF M15 - Heraklion | 11/29 09:00 | 62 | Ioannis Kountourakis v Elmer Moller | 7-5,3-6,10-8 | |
| ITF M15 - Heraklion | 11/23 08:30 | 25 | Kai Wehnelt v Ioannis Kountourakis | 6-3,6-3 | |
| ITF M15 - Heraklion | 11/14 11:00 | 62 | Raffael Schaer v Ioannis Kountourakis | 6-4,6-2 | |
| ITF M15 - Heraklion | 11/08 09:00 | 62 | Zsombor Velcz v Ioannis Kountourakis | 7-5,6-0 | |
| ITF M15 - Heraklion | 11/03 12:40 | 25 | Ioannis Kountourakis v Mark Lajal | 6-4,1-6,2-6 | |
| ITF M15 - Heraklion | 11/02 07:00 | 62 | Jonathan Backman v Ioannis Kountourakis | 6-1,6-7,7-10 | |
| ITF M15 - Heraklion | 11/01 11:00 | 62 | Ioannis Kountourakis v Nikolas Moceanu | 6-1,6-2 | |
| ITF M15 - Cairo | 09/13 08:00 | 62 | Ioannis Kountourakis v Maikel De Boes | 4-6,4-6 | |
| ITF M15 - Cairo | 09/07 07:30 | 62 | Tobias Franco v Ioannis Kountourakis | 6-4,6-2 | |
| ITF M15 - Cairo | 09/06 08:30 | 62 | Antonio Mazzeo v Ioannis Kountourakis | 2-6,4-6 | |
| ITF M15 - Cairo | 09/05 07:30 | 62 | Ioannis Kountourakis v Atharva Sharma | 6-4,6-3 | |
| ITF M15 - Cairo | 08/30 09:00 | 62 | Louis Allen v Ioannis Kountourakis | 6-7,6-4,10-6 | |
| ITF M15 - L'Aquila | 07/11 07:00 | 44 | Ioannis Kountourakis v Federico Bertuccioli | 3-6,4-6 | |
| ITF M15 - Heraklion | 06/08 08:00 | 25 | Petros Tsitsipas v Ioannis Kountourakis | 6-1,7-6 | |
| ITF M15 - Heraklion | 05/30 11:00 | 62 | Eduardo Cohen v Ioannis Kountourakis | 4-6,6-0,10-7 | |
| ITF M15 - Heraklion | 05/23 06:30 | 62 | Ioannis Kountourakis v Christos Avraam | 6-1,4-6,7-10 |