Estadio: Centre Court Round: 26 Ground: Hardcourt outdoor
| ITF W25 Cairns | 2019/09/18 03:45 | Maddison Inglis v Gabriella Da Silva Fick | 6-2,6-2 |
| US Open - Femenino | 2019/08/21 16:55 | Maddison Inglis v Lizette Cabrera | 3-6,0-6 |
| US Open - Femenino | 2019/08/19 15:00 | Maddison Inglis v Valentini Grammatikopoulou | 6-3,6-4 |
| ITF W100 Vancouver | 2019/08/16 19:35 | Maddison Inglis v Heather Watson | 3-6,2-6 |
| ITF W100 Vancouver | 2019/08/15 18:35 | Maddison Inglis v Asia Muhammad | 2-6,7-6,6-4 |
| ITF W80 Granby | 2019/07/26 23:00 | Leylah Annie Fernandez v Maddison Inglis | 6-3,6-4 |
| ITF W80 Granby | 2019/07/25 15:35 | Elizabeth Halbauer v Maddison Inglis | 7-6,6-7,4-6 |
| ITF W80 Granby | 2019/07/24 20:40 | Andreea Ghitescu v Maddison Inglis | 4-6,5-7 |
| 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 W25 Guayaquil | 2019/08/20 15:00 | Alexandra Osborne v Jacqueline Payne | 6-0,6-0 |
| ITF W25 Guayaquil | 2019/08/14 21:05 | Emily Fanning v Alexandra Osborne | 6-0,6-3 |
| ITF W25 Fort Worth | 2019/07/31 16:20 | Alexandra Osborne v Andrea R Villarreal | 3-6,7-6,3-6 |
| ITF W25 Fort Worth | 2019/07/30 14:00 | Alexandra Osborne v Kylie Mckenzie | 6-4,6-2 |