Stadium: Court 3 Round: 28 Ground: Clay
| ITF M15 Prijedor | 2022/05/20 12:10 | Kalin Ivanovski v Oleksandr Ovcharenko | 3-6,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/12 08:00 | Cezar Cretu v Oleksandr Ovcharenko | 4-6,7-5,5-7 |
| ITF M25 Kursumlijska Banja | 2023/05/11 10:50 | Juan Pablo Paz v Oleksandr Ovcharenko | 6-1,3-6,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/09 12:15 | Petar Belosevic v Oleksandr Ovcharenko | 0-6,0-6 |
| ITF M15 Kursumlijska Banja | 2023/05/05 07:30 | Marko Topo v Oleksandr Ovcharenko | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/04 09:05 | Stefan Popovic v Oleksandr Ovcharenko | 5-7,0-6 |
| ITF M15 Kursumlijska Banja | 2023/05/03 07:00 | Luca Teboul v Oleksandr Ovcharenko | 0-6,0-6 |
| Challenger Barletta | 2023/04/02 09:20 | Oleksandr Ovcharenko v Maks Kasnikowski | 5-7,4-6 |
| ITF M15 Opatija | 2023/03/22 08:30 | Oleksandr Ovcharenko v Sergi Perez Contri | 6-7,1-6 |
| ITF M25 Kursumlijska Banja | 2023/05/12 08:00 | Kalin Ivanovski v Hady Habib | 7-6,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | Timo Legout v Kalin Ivanovski | 6-2,1-6,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:00 | Kalin Ivanovski v Viktor Jovic | 3-6,6-3,6-4 |
| Challenger Prague | 2023/05/01 13:00 | Kalin Ivanovski v Dominic Stephan Stricker | 2-6,2-6 |
| Challenger Oeiras | 2023/04/16 12:30 | Billy Harris v Kalin Ivanovski | 6-2,4-6,6-4 |
| Challenger Split | 2023/04/11 12:20 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 |
| ITF M25 Dubrovnik | 2023/04/06 08:00 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 |
| ITF M25 Dubrovnik | 2023/04/05 07:00 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 |