Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Kursumlijska Banja | 2023/05/16 06:55 | Milan Drinic v Nikola Mitrovic | 6-1,6-2 |
| ITF M25 Kursumlijska Banja | 2023/05/15 07:00 | Milan Drinic v Pavle Daljev | 7-5,6-4 |
| UTR Pro Beograd | 2023/04/15 09:52 | Milan Drinic v Stefan Popovic | 1-6,1-6 |
| UTR Pro Beograd | 2023/04/14 07:00 | Milan Drinic v Kristian Juhas | 3-6,6-1,6-4 |
| UTR Pro Beograd | 2023/04/12 08:00 | Milan Drinic v Aleksa Pisaric | 6-4,2-6,6-3 |
| UTR Pro Beograd | 2023/04/11 09:00 | Milan Drinic v Petr Nesterov | 3-6,3-6 |
| ITF M25 Opatija | 2023/03/19 08:00 | Milan Drinic v Maks Lukman | 6-7,6-2,10-12 |
| ITF M15 Rovinj | 2023/03/16 09:00 | Federico Arnaboldi v Milan Drinic | 7-6,7-6 |
| ITF M25 Kursumlijska Banja | 2023/05/16 10:05 | Timofey Stepanov v Luka Todorovic | 6-4,6-3 |
| ITF M25 Kursumlijska Banja | 2023/05/15 08:10 | Timofey Stepanov v Darko Kolevski | 6-0,6-3 |
| ITF M25 Santa Margherita | 2023/04/25 12:25 | Mick Veldheer v Timofey Stepanov | 6-3,1-6,6-1 |
| ITF M25 Santa Margherita | 2023/04/24 08:00 | Timofey Stepanov v Alexander F-R Fragasso | 6-2,6-4 |
| ITF M25 Santa Margherita | 2023/04/23 11:00 | Timofey Stepanov v Umberto Maria Giovannini | 6-3,6-1 |
| ITF M25 Santa Margherita | 2023/04/16 08:30 | Giammarco Gandolfi v Timofey Stepanov | 6-2,7-6 |
| ITF M25 Trnava | 2023/03/28 09:50 | Tomas Vaise v Timofey Stepanov | 6-2,7-5 |
| ITF M25 Trnava | 2023/03/27 13:00 | Ying Hou v Timofey Stepanov | 2-6,2-6 |