Stadium: Court 2 Round: 26 Ground: Clay
| ITF - W15 Antalya | 2023/04/06 09:20 | Olyanovskaya, Valeriya v Tamara Curovic | 7-5,6-4 |
| ITF W25 Varna | 2023/09/12 08:50 | Olyanovskaya, Valeriya v Maria Andrienko | 6-1,6-0 |
| ITF W25 Varna | 2023/09/11 09:15 | Julia Stamatova v Olyanovskaya, Valeriya | 6-3,4-6,7-10 |
| ITF W25 Varna | 2023/09/10 06:00 | Alexandra Azarko v Olyanovskaya, Valeriya | 3-6,0-6 |
| ITF W25 Frydek Mistek | 2023/09/06 08:00 | Isabella Shinikova v Olyanovskaya, Valeriya | 6-3,6-2 |
| ITF W25 Frydek Mistek | 2023/09/05 10:45 | Olyanovskaya, Valeriya v Moravcova, Adela | 4-6,6-4,10-5 |
| ITF W25 Bydgoszcz | 2023/08/25 09:15 | Olyanovskaya, Valeriya v Weronika Falkowska | 6-3,6-7,2-6 |
| ITF W25 Bydgoszcz | 2023/08/23 11:50 | Ilay Yoruk v Olyanovskaya, Valeriya | 1-6,3-6 |
| ITF W25 Bydgoszcz | 2023/08/22 10:30 | Olyanovskaya, Valeriya v Daria Gorska | 6-2,6-0 |
| ITF W25 Varna | 2023/09/13 08:20 | Tamara Curovic v Carolina Kuhl | 6-2,6-2 |
| ITF - W15 Kursumlijska Banja | 2023/09/10 08:00 | Tamara Curovic v Dunja Maric | 2-6,6-2,6-4 |
| ITF - W15 Kursumlijska Banja | 2023/09/09 08:00 | Tamara Curovic v Madelief Hageman | 6-4,6-3 |
| ITF - W15 Kursumlijska Banja | 2023/09/08 08:00 | Tamara Curovic v Kateryna Lazarenko | 6-3,6-2 |
| ITF - W15 Kursumlijska Banja | 2023/09/07 09:15 | Tamara Curovic v Anastasija Cvetkovic | 6-4,6-2 |
| ITF - W15 Kursumlijska Banja | 2023/09/05 15:45 | Tamara Curovic v Karine Sarkisova | 6-4,6-2 |
| ITF - W15 Kursumlijska Banja | 2023/08/31 09:00 | Tamara Curovic v Gebriela Mihaylova | 1-6,3-6 |
| ITF - W15 Kursumlijska Banja | 2023/08/30 09:45 | Tamara Curovic v Sara Mikaca | 6-1,6-1 |