Stadium: Court 5 Round: 62 Ground: Clay
| ITF W25 Bydgoszcz | 2021/08/02 08:00 | Sina Herrmann v Christina Rosca | 6-1,6-2 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/26 10:40 | Dagan Fruchtman, Mika v Sina Herrmann | 1-6,6-4,10-8 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/25 12:00 | Sowjanya Bavisetti v Sina Herrmann | 1-6,1-6 |
| ITF W25 Tarvisio | 2021/07/13 11:50 | Sina Herrmann v Cristina Dinu | 2-6,0-6 |
| WTA Hamburg | 2021/07/05 10:55 | Sina Herrmann v Isabella Shinikova | 4-6,2-6 |
| ITF W25 Wroclaw | 2021/06/29 11:15 | Sina Herrmann v Valeriya Strakhova | 1-6,1-6 |
| ITF W25 Klosters | 2021/06/25 07:00 | Sina Herrmann v Ylena In-Albon | 4-6,2-6 |
| ITF W25 Klosters | 2021/06/24 08:40 | Sina Herrmann v Celine Naef | 6-3,6-3 |
| ITF W25 Bydgoszcz | 2021/08/02 08:00 | Marcelina Podlinska v Olyanovskaya, Valeriya | 4-6,6-4,3-10 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/28 09:40 | Su Jeong Jang v Olyanovskaya, Valeriya | 6-4,6-2 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/27 08:45 | Alice Rame v Olyanovskaya, Valeriya | 3-6,6-2,14-12 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/26 09:20 | Sapfo Sakellaridi v Olyanovskaya, Valeriya | 2-6,1-6 |
| ITF W60 Grodzisk Mazowiecki | 2021/07/25 09:40 | Olyanovskaya, Valeriya v Nuria Brancaccio | 3-6,6-4,10-6 |
| WTA Gdynia | 2021/07/19 10:50 | Olyanovskaya, Valeriya v Anna Bondar | 5-7,3-6 |
| ITF W25 Wroclaw | 2021/06/29 13:20 | Anastasiya Konstantinovna Soboleva v Olyanovskaya, Valeriya | 6-1,6-1 |
| ITF W25 Wroclaw | 2021/06/28 08:00 | Olyanovskaya, Valeriya v Ingrid Vojcinakova | 6-3,6-4 |