Stadium: Court 8 Round: 54 Ground: Hardcourt outdoor
| Orlando, Singles Qualifying W-ITF-USA-27A | 2019/06/18 13:00 | Anna Rogers v Ma, Connie | 2-6,6-3,2-6 |
| Wesley Chapel, Singles Qualifying W-ITF-USA-26A | 2019/06/14 13:00 | Allura Zamarripa v Anna Rogers | 6-3,6-3 |
| Wesley Chapel, Singles Qualifying W-ITF-USA-26A | 2019/06/13 14:35 | Anna Rogers v Mar, Tricia | 6-0,6-1 |
| Wesley Chapel, Singles Qualifying W-ITF-USA-26A | 2019/06/12 14:30 | Anna Rogers v Adesuwa Osabuohien | 6-2,6-1 |
| Sumter, Singles Qualifying W-WITF-USA-18A | 2018/06/10 13:00 | Anna Rogers v Alycia Parks | 1-6,2-6 |
| ITF W15 Cancun | 2019/07/15 14:30 | Sysoeva, Anastasia v Chikalkina, Anastasia | 2-6,6-0,3-10 |
| ITF W15 Cancun | 2019/07/09 16:25 | Chikalkina, Anastasia v Weedon, Kirsten-Andrea | 0-6,1-6 |
| ITF W15 Cancun | 2019/07/01 18:30 | Chikalkina, Anastasia v Verden Anderson, Camille | 3-6,2-6 |
| Khimki, Singles W-ITF-RUS-04A | 2019/04/29 07:00 | Chikalkina, Anastasia v Husaric, Anita | 2-6,0-6 |
| Sharm El Sheikh, Singles W-WITF-EGY-09A | 2018/10/31 11:45 | Chikalkina, Anastasia v Eliz Maloney | 6-4,3-6,3-6 |
| Sharm El Sheikh, Singles W-WITF-EGY-09A | 2018/10/29 08:00 | Chantraine, Elisabeth v Chikalkina, Anastasia | 2-6,2-6 |
| Moscow, Singles W-WITF-RUS-05A | 2018/08/27 08:40 | Kruzhkova, Daria v Chikalkina, Anastasia | 7-5,6-2 |
| Moscow, Singles W-WITF-RUS-05A | 2018/08/26 07:00 | Chikalkina, Anastasia v Evgeniya Burdina | 7-6,6-3 |