Estadio: Court Bucks (13) Round: 25 Ground: Hardcourt outdoor
| WTA Columbus | 2021/09/22 00:30 | Maddison Inglis v Louisa Chirico | 3-6,6-1,2-6 |
| ITF W80 Macon | 2021/10/19 16:00 | Alycia Parks v Louisa Chirico | 3-6,6-7 |
| ITF W80 Macon | 2021/10/18 15:00 | Reese Brantmeier v Louisa Chirico | 6-4,4-6,7-10 |
| ITF W60 Las Vegas | 2021/10/07 17:00 | Louisa Chirico v Allie Kiick | 6-3,3-6,6-7 |
| ITF W60 Las Vegas | 2021/10/05 21:00 | Louisa Chirico v Jessie Aney | 6-4,4-6,7-6 |
| ITF W60 Berkeley | 2021/10/01 17:00 | Mayo Hibi v Louisa Chirico | 6-2,6-3 |
| ITF W60 Berkeley | 2021/09/28 20:30 | Louisa Chirico v Panna Udvardy | 6-4,4-6,6-4 |
| WTA Columbus | 2021/09/23 19:30 | Madison Brengle v Louisa Chirico | 6-4,6-4 |
| WTA Columbus | 2021/09/22 00:30 | Maddison Inglis v Louisa Chirico | 3-6,6-1,2-6 |
| ITF W60 Rancho Santa Fe | 2021/10/13 18:45 | Rebecca Marino v Maddison Inglis | 6-4,6-3 |
| WTA Indian Wells | 2021/10/05 19:35 | Maddison Inglis v Alycia Parks | 3-6,4-6 |
| WTA Indian Wells | 2021/10/04 19:15 | Maddison Inglis v Mariam Bolkvadze | 7-6,6-2 |
| WTA Chicago | 2021/09/29 14:00 | Belinda Bencic v Maddison Inglis | 5-7,6-1,6-0 |
| WTA Chicago | 2021/09/27 16:45 | Maddison Inglis v Caroline Dolehide | 4-6,6-2,6-4 |
| WTA Chicago | 2021/09/26 15:00 | Maddison Inglis v Asia Muhammad | 6-7,6-4,7-6 |
| WTA Chicago | 2021/09/25 15:00 | Maddison Inglis v Julia Lohoff | 6-2,6-2 |
| WTA Columbus | 2021/09/22 00:30 | Maddison Inglis v Louisa Chirico | 3-6,6-1,2-6 |