Stadium: Court 4 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M25 Heraklion | 2022/11/21 08:00 | Milan Drinic v Ioannis Kountourakis | 7-5,7-6 |
| ITF M15 Sharm El Sheikh | 2024/02/04 08:00 | Ioannis Kountourakis v Matthew Summers | 7-6,7-6 |
| ITF M15 Sharm El Sheikh | 2024/01/31 11:30 | Ioannis Kountourakis v Mark Whitehouse | 6-7,6-3,1-6 |
| ITF M15 Sharm El Sheikh | 2024/01/30 10:05 | Ioannis Kountourakis v Filiberto Fumagalli | 6-1,3-6,10-5 |
| ITF M15 Sharm El Sheikh | 2024/01/29 11:30 | Ioannis Kountourakis v Tsihon Fedorov | 6-3,6-4 |
| ITF M15 Sharm El Sheikh | 2024/01/28 08:00 | Ioannis Kountourakis v Kiyan Santino Kasemi | 6-1,6-0 |
| ITF M15 Cadolzburg | 2024/01/17 11:40 | Leopold Zima v Ioannis Kountourakis | 6-2,6-2 |
| ITF M15 Cadolzburg | 2024/01/15 10:00 | Ioannis Kountourakis v Mihailo Milenkovic | 6-4,6-1 |
| ITF M15 Cadolzburg | 2024/01/14 11:30 | Ioannis Kountourakis v Tobias Brutscher | 6-4,6-1 |
| ITF M15 Sharm El Sheikh | 2024/02/04 12:00 | Bader Alabdullah v Milan Drinic | 5-7,3-6 |
| UTR Pro Dubai | 2023/11/26 05:00 | Christos Keisidis v Milan Drinic | 3-6,1-3 |
| UTR Pro Dubai | 2023/11/25 08:00 | Dragos Constantin Ignat v Milan Drinic | 3-6,2-6 |
| UTR Pro Dubai | 2023/11/23 07:53 | Milan Drinic v Lazar Vojinovic | 2-6,7-5,5-7 |
| UTR Pro Dubai | 2023/11/22 09:01 | Milan Drinic v Evgeny Karlovskiy | 4-6,6-1,3-6 |
| UTR Pro Dubai | 2023/11/21 07:20 | Milan Drinic v Benedikt Henning | 3-6,4-6 |
| UTR Pro Dubai | 2023/11/20 05:00 | Milan Drinic v Lun Obrul | 6-2,6-1 |
| UTR Pro Dubai | 2023/11/18 11:38 | Charles Bertimon v Milan Drinic | 7-6,6-2 |