Stadium: Court 2 Round: 24 Ground: Hardcourt outdoor
| 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 |
| ITF W60 Caldas da Rainha | 2021/09/18 15:00 | Saisai Zheng v Maddison Inglis | 6-2,6-3 |
| ITF W60 Caldas da Rainha | 2021/09/17 15:15 | Maddison Inglis v Anastasia Kulikova | 6-2,4-6,6-3 |
| ITF W60 Caldas da Rainha | 2021/09/16 09:00 | Maddison Inglis v Natalija Stevanovic | 6-2,6-1 |
| ITF W60 Caldas da Rainha | 2021/09/14 12:05 | Maddison Inglis v Weronika Falkowska | 3-6,7-5,6-3 |
| US Open - Kvinner | 2021/08/24 21:40 | Monica Niculescu v Maddison Inglis | 6-4,6-7,6-2 |
| WTA Columbus | 2021/09/19 22:10 | Caroline Dolehide v Renata Zarazua | 4-6,6-1,6-7 |
| US Open - Kvinner | 2021/08/27 23:30 | Caroline Dolehide v Olga Danilovic | 4-6,6-0,2-6 |
| US Open - Kvinner | 2021/08/26 23:00 | Caroline Dolehide v Victoria Duval | 5-7,6-4,6-3 |
| US Open - Kvinner | 2021/08/25 22:15 | Irina Maria Bara v Caroline Dolehide | 4-6,1-6 |
| WTA - Chicago | 2021/08/17 17:35 | Caroline Dolehide v Storm Hunter | 3-6,6-4,2-6 |
| WTA - Chicago | 2021/08/16 16:00 | Lesley Pattinama Kerkhove v Caroline Dolehide | 6-2,2-6,3-6 |
| ITF W100 Landisville | 2021/08/11 15:45 | Caroline Dolehide v Mayo Hibi | 4-6,4-6 |
| WTA Concord | 2021/08/05 20:50 | Caroline Dolehide v Katrina Scott | 6-1,0-6,5-7 |