Stadium: Hard 17 Round: 25 Ground: Hardcourt outdoor
| ITF M15 - Heraklion | 2023/10/20 07:00 | Guy Den Ouden v Jakub Nicod | 2-6,6-7 |
| ITF M15 - Heraklion | 2023/10/19 08:45 | Dax Donders v Guy Den Ouden | 6-7,5-7 |
| ITF M15 - Heraklion | 2023/10/18 07:25 | Guy Den Ouden v Matthew William Donald | 6-4,6-2 |
| ITF M15 - Heraklion | 2023/10/17 06:30 | Guy Den Ouden v David Quayle | 6-1,7-5 |
| ITF M15 - Heraklion | 2023/10/16 07:00 | Guy Den Ouden v Hamid Reza Nadaf | 6-3,6-4 |
| ITF M25 - Koksijde | 2023/08/20 13:00 | Guy Den Ouden v Timo Legout | 7-5,6-2 |
| ITF M25 - Koksijde | 2023/08/19 12:00 | Luciano Emanuel Ambrogi v Guy Den Ouden | 3-6,4-6 |
| ITF M25 - Koksijde | 2023/08/18 08:00 | Guy Den Ouden v Buvaysar Gadamauri | 6-3,7-5 |
| ITF M15 - Heraklion | 2023/10/19 06:30 | Ioannis Kountourakis v Sidane Pontjodikromo | 4-6,6-2,2-6 |
| ITF M15 - Heraklion | 2023/10/18 08:10 | Ki Lung NG v Ioannis Kountourakis | 3-6,3-6 |
| ITF M15 - Heraklion | 2023/10/17 06:30 | Ioannis Kountourakis v Gabriel Matuszewski | 6-3,6-0 |
| ITF M15 - Heraklion | 2023/10/16 09:00 | Ioannis Kountourakis v Piotr Siekanowicz | 6-3,6-0 |
| ITF M15 - Kursumlijska Banja | 2023/09/21 12:30 | Ioannis Kountourakis v Stefan Popovic | 2-6,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/19 08:45 | Marko Nikolic v Ioannis Kountourakis | 4-6,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/18 11:00 | Aleksandar Mihailovic v Ioannis Kountourakis | 1-6,6-7 |