Stadium: Court 5 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Skopje | 2022/06/06 12:15 | Ioannis Kountourakis v Matic Dimic | 7-5,4-6,10-8 |
| ITF M15 Sharm El Sheikh | 2023/02/12 10:00 | Ioannis Kountourakis v Pietro Schiavetti | 6-3,3-6,10-6 |
| ITF M15 Monastir | 2023/01/30 10:15 | Andrew Rogers v Ioannis Kountourakis | 7-5,6-2 |
| ITF M15 Monastir | 2023/01/29 09:00 | Anthony Shumsky v Ioannis Kountourakis | 2-6,0-6 |
| ITF M15 Monastir | 2023/01/22 10:30 | Ioannis Kountourakis v Erik Arutiunian | 2-6,6-7 |
| ITF M15 Monastir | 2023/01/15 11:30 | Ioannis Kountourakis v Alessandro Ragazzi | 6-3,6-7,8-10 |
| ITF M15 Monastir | 2022/12/26 08:00 | Mohamed Ali Abibsi v Ioannis Kountourakis | 4-6,7-5,10-7 |
| ITF M15 Monastir | 2022/12/18 10:00 | Mikail Alimli v Ioannis Kountourakis | 6-4,6-2 |
| ITF M25 Heraklion | 2022/11/21 08:00 | Milan Drinic v Ioannis Kountourakis | 7-5,7-6 |
| ITF M15 Sharm El Sheikh | 2023/02/12 11:30 | Matic Dimic v Roland Stuurman | 6-3,1-6,10-3 |
| ITF M15 Sharm El Sheikh | 2023/02/05 08:00 | Matic Dimic v Tomas Lanik | 3-6,6-3,4-10 |
| ITF M15 Sharm El Sheikh | 2023/02/01 08:00 | Matic Dimic v Ammar Faleh Alhogbani | 4-6,2-6 |
| ITF M15 Antalya | 2022/10/30 07:00 | Alfred Almasi v Matic Dimic | 6-4,7-6 |
| ITF M15 Antalya | 2022/10/24 10:55 | Matic Dimic v Cengiz Aksu | 0-6,1-6 |
| ITF M15 Antalya | 2022/10/23 07:00 | Gal Emersic Potocnik v Matic Dimic | 0-6,2-6 |
| ITF M15 Sozopol | 2022/10/09 10:00 | Piotr Czaczkowski v Matic Dimic | 7-5,7-5 |
| ITF M15 Sozopol | 2022/10/04 11:20 | Vladyslav Orlov v Matic Dimic | 6-1,7-6 |