| UTR Pro Pozos | 2023/01/09 19:00 | Milan Drinic v Eduardo Yahir Orozco Rangel | 7-6,6-7,6-4 |
| UTR Pro Tennis Series Dubai | 2022/12/11 06:30 | Milan Drinic v Alen Moritz Hodzic | 6-3,6-1 |
| UTR Pro Tennis Series Dubai | 2022/12/10 08:00 | Savriyan Danilov v Milan Drinic | 2-3 |
| UTR Pro Tennis Series Dubai | 2022/12/09 08:22 | Milan Drinic v Mikalai Haliak | 7-6,6-4 |
| UTR Pro Tennis Series Dubai | 2022/12/07 06:30 | Milan Drinic v Ivan Denisov | 4-6,3-6 |
| UTR Pro Tennis Series Dubai | 2022/12/06 06:30 | Milan Drinic v Matyas Fuele | 5-7,6-2,3-6 |
| UTR Pro Tennis Series Dubai | 2022/12/05 08:00 | Bogdan Bobrov v Milan Drinic | 6-3,6-1 |
| ITF M25 Heraklion | 2022/11/22 08:30 | Francois Musitelli v Milan Drinic | 6-4,6-4 |
| UTR Pro Pozos | 2023/01/09 20:30 | Kyle Overmyer v Manuel S Montemayor | 1-6,1-6 |
| ITF M25 Norman | 2022/10/24 06:00 | Piotr Pawlak v Kyle Overmyer | 6-4,6-3 |
| ITF M15 Albuquerque | 2022/09/26 15:00 | Nico Mostardi v Kyle Overmyer | 6-0,3-6,10-7 |
| ITF M15 Lubbock | 2022/09/19 14:00 | Kyle Overmyer v Marcus Walters | 4-6,4-6 |
| ITF M25 Columbus | 2022/08/09 13:00 | Alexander Petrov v Kyle Overmyer | 6-0,6-0 |
| ITF M15 Lakewood | 2022/07/11 16:00 | Kyle Overmyer v John B D Otico | 5-7,2-6 |
| ITF M15 Lakewood | 2022/07/10 18:30 | Calvin Thalheimer v Kyle Overmyer | 4-6,3-6 |
| ITF M15 Los Angeles | 2022/06/26 17:00 | Kyle Overmyer v Nikolay Sysoev | 7-6,0-6,5-10 |