Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF W25 - Cairns | 2019/09/19 02:15 | Maddison Inglis v Alexandra Osborne | 6-2,6-3 |
| ITF W60 - Darwin | 2019/09/25 05:15 | Ho Ching Wu v Alexandra Osborne | 6-4,6-4 |
| ITF W60 - Darwin | 2019/09/24 00:30 | Tereza Mihalikova v Alexandra Osborne | 7-5,1-6,6-10 |
| ITF W60 - Darwin | 2019/09/23 00:30 | Ya Yun Pai v Alexandra Osborne | 5-7,0-6 |
| ITF W25 - Cairns | 2019/09/19 02:15 | Maddison Inglis v Alexandra Osborne | 6-2,6-3 |
| ITF W25 - Cairns | 2019/09/17 06:30 | Olivia Symons v Alexandra Osborne | 5-7,5-7 |
| ITF W25 - Guayaquil | 2019/08/23 15:30 | Alexandra Osborne v Maria Camila Osorio | 6-4,5-7,4-6 |
| ITF W25 - Guayaquil | 2019/08/22 15:00 | Alexandra Osborne v Yuliana Lizarazo | 7-6,2-6,6-4 |
| ITF W25 - Guayaquil | 2019/08/21 17:05 | Barbara Gatica v Alexandra Osborne | 4-6,6-3,5-7 |
| ITF W60 - Darwin | 2019/09/27 00:30 | Asia Muhammad v Maddison Inglis | 6-1,6-4 |
| ITF W60 - Darwin | 2019/09/26 03:05 | Chihiro Muramatsu v Maddison Inglis | 0-6,1-6 |
| ITF W60 - Darwin | 2019/09/25 02:25 | Haruna Arakawa v Maddison Inglis | 4-6,0-6 |
| ITF W25 - Cairns | 2019/09/21 01:30 | Maddison Inglis v Asia Muhammad | 4-6,0-6 |
| ITF W25 - Cairns | 2019/09/20 03:00 | Maddison Inglis v Haruna Arakawa | 6-3,6-2 |
| ITF W25 - Cairns | 2019/09/19 02:15 | Maddison Inglis v Alexandra Osborne | 6-2,6-3 |
| ITF W25 - Cairns | 2019/09/18 03:45 | Maddison Inglis v Gabriella Da Silva Fick | 6-2,6-2 |
| US Open - Damer | 2019/08/21 16:55 | Maddison Inglis v Lizette Cabrera | 3-6,0-6 |