| ITF M15 Sharm El Sheikh | 02/19 11:30 | 62 | Ioannis Kountourakis v Ioan A Teglas | 6-3,7-5 | |
| ITF M15 Sharm El Sheikh | 02/14 08:00 | 62 | Sebastian Sorger v Ioannis Kountourakis | 6-4,6-3 | |
| ITF M15 Sharm El Sheikh | 02/13 08:00 | 62 | Ioannis Kountourakis v Matic Dimic | 7-5,0-6,10-8 | |
| ITF M15 Sharm El Sheikh | 02/12 10:00 | 62 | Ioannis Kountourakis v Pietro Schiavetti | 6-3,3-6,10-6 | |
| ITF M15 Monastir | 01/30 10:15 | 54 | Andrew Rogers v Ioannis Kountourakis | 7-5,6-2 | |
| ITF M15 Monastir | 01/29 09:00 | 54 | Anthony Shumsky v Ioannis Kountourakis | 2-6,0-6 | |
| ITF M15 Monastir | 01/22 10:30 | 62 | Ioannis Kountourakis v Erik Arutiunian | 2-6,6-7 | |
| ITF M15 Monastir | 01/15 11:30 | 62 | Ioannis Kountourakis v Alessandro Ragazzi | 6-3,6-7,8-10 | |
| ITF M15 Monastir | 12/26 08:00 | 62 | Mohamed Ali Abibsi v Ioannis Kountourakis | 4-6,7-5,10-7 | |
| ITF M15 Monastir | 12/18 10:00 | 62 | Mikail Alimli v Ioannis Kountourakis | 6-4,6-2 | |
| ITF M25 Heraklion | 11/21 08:00 | 62 | Milan Drinic v Ioannis Kountourakis | 7-5,7-6 | |
| ITF M25 Heraklion | 11/14 07:30 | 62 | Ioannis Kountourakis v Damian Rodriguez | 4-6,2-6 | |
| ITF M25 Heraklion | 11/13 08:30 | 62 | Ioannis Kountourakis v Adi Dagan | 6-3,6-2 | |
| ITF M15 Heraklion | 11/08 11:55 | 25 | Sebastian Gima v Ioannis Kountourakis | 3-6,6-1,6-3 | |
| ITF M15 Heraklion | 11/02 12:20 | 25 | Ioannis Kountourakis v Tao Mu | 5-7,1-6 | |
| ITF M15 Kottingbrunn | 08/01 10:00 | 44 | Ioannis Kountourakis v Vojtech Vlkovsky | 4-6,4-6 | |
| ITF M15 Kottingbrunn | 07/31 10:30 | 44 | Ioannis Kountourakis v Nico Jaeger | 6-2,7-5 | |
| ITF M25 Kottingbrunn | 07/25 07:30 | 44 | Ioannis Kountourakis v Leonardo Catani | 6-7,6-0,6-10 | |
| ITF M25 Kottingbrunn | 07/24 07:00 | 44 | Ioannis Kountourakis v Marcell Bartakovics | 6-4,6-4 | |
| ITF M25 Roehampton | 07/10 11:35 | 54 | Scott Duncan v Ioannis Kountourakis | 6-1,6-4 | |
| ITF M15 Sofia | 07/04 12:30 | 44 | Ioannis Kountourakis v Tuncay Duran | 5-7,6-4,6-10 | |
| ITF M15 Sofia | 07/04 08:00 | 44 | Mihail Ivanov v Ioannis Kountourakis | 6-4,4-6,8-10 | |
| ITF M15 Sofia | 07/03 09:00 | 44 | William Alsterback v Ioannis Kountourakis | 1-6,1-6 | |
| ITF M25 Skopje | 06/07 07:55 | 62 | Tomislav Jotovski v Ioannis Kountourakis | 6-2,6-0 | |
| ITF M25 Skopje | 06/06 12:15 | 62 | Ioannis Kountourakis v Matic Dimic | 7-5,4-6,10-8 | |
| ITF M25 Skopje | 06/05 08:00 | 62 | Ioannis Kountourakis v Stevan Popovic | 6-3,6-3 | |
| 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 |