Round: 54 Ground: Hardcourt outdoor
| ITF W40 Γουαδαλαχάρα | 2016/09/25 02:30 | Μαριάνα Ζάκαρλιουκ v Brooke Winley | 6-2,6-2 |
| ITF W40 Γουαδαλαχάρα | 2016/09/25 00:00 | Somer Dalla-Bona v Brooke Winley | 2-6,4-6 |
| ITF Women Tweed Heads Qual | 2016/09/19 01:40 | Γκαμπριέλλα Ντα Σίλβα Φίκ v Brooke Winley | 7-6,6-4 |
| ITF Women Tweed Heads Qual | 2016/09/18 01:00 | Brooke Winley v Tayla Whitehouse | 6-3,6-0 |
| ITF Women Hong Kong | 2016/07/16 05:30 | Άγιανο Σίμιζου v Brooke Winley | 6-1,6-2 |
| ITF Women Hong Kong | 2016/07/09 05:00 | Μικαέλα Χάετ v Brooke Winley | 6-3,7-5 |
| ITF Women Canberra Qual | 2016/03/12 23:00 | Katharina Lehnert v Brooke Winley | 6-4,6-1 |
| ITF Women Bendigo Qual | 2016/10/23 23:00 | Genevieve Lorbergs v Anne-Marie Medcalf | 7-6,6-3 |
| ITF Women Bendigo Qual | 2016/10/22 22:30 | Anne-Marie Medcalf v Viktorija Rajicic | 6-3,4-6,6-3 |
| ITF Women Cairns Qual | 2016/10/10 01:00 | Sandra Zaniewska v Anne-Marie Medcalf | 6-0,6-1 |
| ITF Women Cairns Qual | 2016/10/09 01:00 | Anne-Marie Medcalf v Kirijana Petreski | 7-6,7-6 |
| ITF Women Toowoomba Qual | 2016/10/02 00:00 | Αλίσια Σμιθ v Anne-Marie Medcalf | 6-3,6-1 |
| ITF Women Tweed Heads | 2016/09/21 03:30 | Viktorija Rajicic v Anne-Marie Medcalf | 6-2,3-6,6-2 |
| ITF Women Tweed Heads Qual | 2016/09/19 01:20 | Anne-Marie Medcalf v Τζιόρτζιε Τζόουνς | 6-1,6-3 |
| ITF Women Tweed Heads Qual | 2016/09/18 01:00 | Ρενέ Μακμπράιντ v Anne-Marie Medcalf | 3-6,6-1,4-6 |