Stadium: Casper Court (Ct 1) Round: 28 Ground: Clay
| ITF W15 Naples | 2019/05/17 15:00 | Woolcock, Belinda v Mara Schmidt | 6-4,6-1 |
| ITF W15 Naples | 2019/05/16 17:35 | Woolcock, Belinda v Victoria Hu | 6-3,6-1 |
| ITF W15 Naples | 2019/05/14 14:00 | Woolcock, Belinda v Wijesundera, Rushri | 6-0,6-1 |
| ITF - W100 Bonita Springs | 2019/05/07 17:05 | Woolcock, Belinda v Fernandez, Leylah Annie | 7-5,3-6,5-10 |
| ITF - W100 Bonita Springs | 2019/05/06 15:30 | Khazaniuk, Deniz v Woolcock, Belinda | 6-0,4-6,5-10 |
| ITF W100 Charleston | 2019/05/02 14:00 | Woolcock, Belinda v Kaja Juvan | 4-6,4-6 |
| ITF W100 Charleston | 2019/05/01 19:40 | Woolcock, Belinda v Rasheeda McAdoo | 6-2,7-6 |
| ITF W100 Charleston | 2019/04/30 14:00 | Neel, Ingrid v Woolcock, Belinda | 3-6,3-6 |
| ITF W15 Naples | 2019/05/17 15:00 | Collins, Kylie v Brantmeier, Reese | 6-3,2-6,6-3 |
| ITF W15 Naples | 2019/05/16 14:00 | Nina Stadler v Collins, Kylie | 6-4,5-7,2-6 |
| ITF W15 Naples | 2019/05/14 14:00 | Collins, Kylie v Blakely, Audrey Ann | 6-7,6-4,6-3 |
| Williamsburg, Singles W-ITF-USA-16B | 2019/05/08 13:30 | Collins, Kylie v Nina Stadler | 5-7,3-6 |
| Williamsburg, Singles W-ITF-USA-16B | 2019/05/07 15:30 | Robin Montgomery v Collins, Kylie | 4-6,4-6 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/24 14:30 | Collins, Kylie v Renata Zarazua | 4-6,2-6 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/23 14:30 | Collins, Kylie v Rhiann Newborn | 3-6,6-2,11-9 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/22 14:30 | Ksenia Laskutova v Collins, Kylie | 5-7,4-6 |