Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF W25 Mildura | 2019/03/06 04:00 | Olivia Rogowska v Belinda Woolcock | 6-4,2-6,5-7 |
| ITF W25 Playford | 2018/12/31 23:30 | Olivia Rogowska v Belinda Woolcock | 6-3,6-7,5-10 |
| ITF Women Penrith | 2017/09/21 02:45 | Belinda Woolcock v Olivia Rogowska | 6-7,6-7 |
| ITF W25 Gatineau | 2019/07/17 16:25 | Sophie Chang v Olivia Rogowska | 6-7,6-4,6-1 |
| ITF W25 Saskatoon | 2019/07/11 17:00 | Madison Westby v Olivia Rogowska | 4-6,6-3,6-3 |
| ITF W25 Saskatoon | 2019/07/10 17:35 | Jessica Livianu v Olivia Rogowska | 6-2,6-7,1-6 |
| ITF W60 Stare Splavy | 2019/06/18 12:55 | Sofya Lansere v Olivia Rogowska | 3-6,7-5,6-2 |
| ITF W60 Torun | 2019/06/04 13:35 | Stefania Rogozinska-Dzik v Olivia Rogowska | 6-4,6-3 |
| ITF W100 Bonita Springs | 2019/05/07 18:55 | Olivia Rogowska v Claire Liu | 5-7,6-3,2-6 |
| ITF W100 Charleston | 2019/04/30 15:30 | Olivia Rogowska v Cori Gauff | 1-6,3-6 |
| ITF W25 Osprey | 2019/04/25 15:55 | Alexa Glatch v Olivia Rogowska | 6-1,6-1 |
| WTA New York | 2019/08/17 14:00 | Jil Teichmann v Belinda Woolcock | 6-3,6-4 |
| WTA New York | 2019/08/16 14:00 | Belinda Woolcock v Nika Kukharchuk | 6-4,7-6 |
| ITF W60 Concord | 2019/08/12 21:00 | Belinda Woolcock v Magdalena Frech | 4-6,5-7 |
| ITF W60 Concord | 2019/08/12 13:00 | Varvara Gracheva v Belinda Woolcock | 6-3,6-7,6-10 |
| ITF W60 Landisville | 2019/08/05 17:35 | Belinda Woolcock v Angelina Gabueva | 4-6,2-6 |
| ITF W60 Lexington | 2019/07/31 23:00 | Belinda Woolcock v Katie Swan | 2-6,1-6 |
| ITF W25 Bethany Beach | 2019/06/06 15:35 | Layne Sleeth v Belinda Woolcock | 2-6,2-6 |
| ITF W25 Bethany Beach | 2019/06/04 16:10 | Pamela Montez v Belinda Woolcock | 0-6,0-6 |