Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| ITF M15 Pirot | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| ITF M15 Pirot | 2023/09/04 07:30 | Ioannis Kountourakis v Lorenzo Vatteroni | 6-2,6-3 |
| ITF M15 Pirot | 2023/09/03 10:00 | Mal Agushi v Ioannis Kountourakis | 5-7,3-6 |
| ITF M15 Kursumlijska Banja | 2023/08/31 11:20 | Ioannis Kountourakis v Dusan Obradovic | 4-6,6-7 |
| ITF M15 Kursumlijska Banja | 2023/08/30 13:45 | Nikola Djosic v Ioannis Kountourakis | 4-6,7-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/08/29 09:45 | Ioannis Kountourakis v Maxim Krapivin | 6-2,6-4 |
| ITF M15 Kursumlijska Banja | 2023/08/28 12:00 | Lorenzo Vatteroni v Ioannis Kountourakis | 6-0,3-6,9-11 |
| ITF M15 Metzingen | 2023/07/23 07:30 | Ioannis Kountourakis v Stepan Mruzek | 3-6,5-7 |
| ITF M15 Monastir | 2023/09/04 09:30 | Max Benaim v Ahmed Mouhan | 6-1,6-0 |
| ITF M25 Aldershot | 2023/08/13 09:00 | Max Benaim v Ewan Moore | 6-4,3-6,14-16 |
| ITF M25 Herzlia | 2023/08/09 12:10 | Ben Weintraub v Max Benaim | 6-0,6-2 |
| ITF M25 Herzlia | 2023/08/08 06:30 | Max Benaim v Mark Neyelov | 4-6,6-1,10-7 |
| ITF M25 Herzlia | 2023/08/07 07:00 | Ido Geva v Max Benaim | 5-7,2-6 |
| ITF M15 Raanana | 2023/07/30 11:30 | Mark Bogdanov v Max Benaim | 1-6,6-3,14-12 |
| ITF M25 Roehampton | 2023/07/16 12:25 | Lorenzo Lorusso v Max Benaim | 6-1,6-7,10-8 |
| ITF M25 Nottingham | 2023/07/09 10:00 | Alexander Klintcharov v Max Benaim | 6-3,6-1 |