Stadium: Court 1 Round: 27 Ground: Clay
| ITF W25 Parnu | 2021/08/05 08:30 | Anna Siskova v Kolar, Nastja | 6-1,6-3 |
| ITF W25 Parnu | 2021/08/04 16:55 | Anna Siskova v Verena Meliss | 6-2,6-4 |
| ITF W60 Olomouc | 2021/07/21 10:35 | Nikola Breckova v Anna Siskova | 6-3,3-6,6-3 |
| ITF W60 Nur-Sultan | 2021/07/15 06:00 | Hatouka, Yuliya v Anna Siskova | 6-2,6-1 |
| ITF W60 Nur-Sultan | 2021/07/14 13:45 | Maria Timofeeva v Anna Siskova | 4-6,5-7 |
| ITF W60 Nur-Sultan | 2021/07/13 06:00 | Anna Siskova v Sukhotina, Anastasia | 6-2,6-4 |
| ITF W25 Nur-Sultan | 2021/07/08 05:00 | Sharipova, Sabina v Anna Siskova | 7-5,6-2 |
| ITF W25 Nur-Sultan | 2021/07/07 05:30 | Anna Siskova v Sofya Lansere | 7-5,6-3 |
| ITF W25 Parnu | 2021/08/05 10:00 | Vehvilainen, Liisa v Gatto-Monticone, Giulia | 0-6,2-6 |
| ITF W25 Parnu | 2021/08/04 07:00 | Anna Ureke v Gatto-Monticone, Giulia | 3-6,1-6 |
| WTA Palermo | 2021/07/19 19:30 | Gatto-Monticone, Giulia v Maddison Inglis | 2-6,3-6 |
| WTA Prague | 2021/07/12 08:00 | Gatto-Monticone, Giulia v Greet Minnen | 0-6,6-4,1-6 |
| WTA Bastad | 2021/07/06 13:55 | Arruabarrena, L. v Gatto-Monticone, Giulia | 6-2,6-3 |
| ITF W25 Palma del Rio | 2021/07/01 19:55 | Gatto-Monticone, Giulia v Rebeka Masarova | 1-6,2-6 |
| ITF W25 Palma del Rio | 2021/06/30 19:20 | Gatto-Monticone, Giulia v Haruka Kaji | 6-3,6-3 |
| Wimbledon Women | 2021/06/23 10:00 | Arina Rodionova v Gatto-Monticone, Giulia | 6-3,6-0 |