Stadium: TSITSIPAS COURT Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2022/11/20 10:00 | Milan Drinic v Gal Emersic Potocnik | 6-0,1-6,10-6 |
| ITF M25 Heraklion | 2022/11/14 07:30 | Milan Drinic v Rocco Piatti | 6-4,4-6,8-10 |
| ITF M25 Heraklion | 2022/11/13 07:00 | Marlon Vankan v Milan Drinic | 2-6,3-6 |
| ITF M15 Heraklion | 2022/11/06 12:00 | Gorazd Srbljak v Milan Drinic | 3-6,6-4,10-8 |
| ITF M15 Heraklion | 2022/11/01 07:30 | Milan Drinic v Henrik Bladelius | 6-4,6-7,8-10 |
| UTR Pro Tennis Series Belgrade | 2022/10/15 08:15 | Oleg Prihodko v Milan Drinic | 6-4,6-3 |
| UTR Pro Tennis Series Belgrade | 2022/10/14 09:00 | Horst Rieder v Milan Drinic | 6-4,4-6,3-6 |
| UTR Pro Tennis Series Belgrade | 2022/10/13 06:00 | Ilya Snitari v Milan Drinic | 6-2,6-4 |
| ITF M25 Heraklion | 2022/11/14 07:30 | Ioannis Kountourakis v Damian Rodriguez | 4-6,2-6 |
| ITF M25 Heraklion | 2022/11/13 08:30 | Ioannis Kountourakis v Adi Dagan | 6-3,6-2 |
| ITF M15 Heraklion | 2022/11/08 11:55 | Sebastian Gima v Ioannis Kountourakis | 3-6,6-1,6-3 |
| ITF M15 Heraklion | 2022/11/02 12:20 | Ioannis Kountourakis v Tao Mu | 5-7,1-6 |
| ITF M15 Kottingbrunn | 2022/08/01 10:00 | Ioannis Kountourakis v Vojtech Vlkovsky | 4-6,4-6 |
| ITF M15 Kottingbrunn | 2022/07/31 10:30 | Ioannis Kountourakis v Nico Jaeger | 6-2,7-5 |
| ITF M25 Kottingbrunn | 2022/07/25 07:30 | Ioannis Kountourakis v Leonardo Catani | 6-7,6-0,6-10 |
| ITF M25 Kottingbrunn | 2022/07/24 07:00 | Ioannis Kountourakis v Marcell Bartakovics | 6-4,6-4 |