Stadium: Court 26/25 Round: 25 Ground: Clay
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/24 17:35 | Montez, Pamela v Woolcock, Belinda | 1-6,6-3,7-5 |
| ITF W100 Charleston | 2019/04/29 18:25 | Montez, Pamela v Sophie Chang | 7-5,3-6,8-10 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/25 14:30 | Montez, Pamela v Renata Zarazua | 1-6,0-6 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/24 17:35 | Montez, Pamela v Woolcock, Belinda | 1-6,6-3,7-5 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/23 16:15 | Montez, Pamela v Rencheli, Abigail | 6-4,6-1 |
| Osprey, Fl, Singles Qualifying W-ITF-USA-14A | 2019/04/22 14:30 | Montez, Pamela v Lea Ma | 6-4,6-4 |
| ITF W15 Cancun | 2019/04/18 17:35 | Natsumi Kawaguchi v Montez, Pamela | 6-0,6-0 |
| ITF W15 Cancun | 2019/04/17 18:20 | Clara Vlasselaer v Montez, Pamela | 7-5,6-7,1-6 |
| Palm Harbor, Fl, Qualifications Simples W-ITF-USA-08A | 2019/04/04 14:00 | Kovinic, Danka v Montez, Pamela | 6-3,6-1 |
| ITF W15 Naples | 2019/05/19 14:30 | Woolcock, Belinda v Stewart, Katerina | 4-6,3-6 |
| ITF W15 Naples | 2019/05/18 16:20 | Woolcock, Belinda v Collins, Kylie | 6-1,6-4 |
| 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 |