Stadium: Court 7 Round: 25 Ground: Hardcourt outdoor
| Carson, Singles W-ITF-USA-06A | 2019/03/05 18:30 | Guillermo, Lorraine M v Westby, Madison | 6-4,6-2 |
| ITF - W15 Monastir | 2019/02/04 08:00 | Westby, Madison v Timsit, Agathe | 7-5,1-6,7-10 |
| ITF - W15 Monastir | 2019/01/29 09:00 | Westby, Madison v Dentoni, Corinna | 2-6,4-6 |
| ITF - W15 Monastir | 2019/01/24 09:30 | Mirjam Bjorklund v Westby, Madison | 6-1,6-1 |
| ITF - W15 Monastir | 2019/01/23 10:50 | Milosevic, Tamara v Westby, Madison | 2-6,2-6 |
| ITF - W15 Monastir | 2019/01/15 09:40 | Westby, Madison v Amy Zhu | 4-6,6-4,4-6 |
| ITF Women Stellenbosch | 2018/12/07 09:00 | Lindh Gallagher, Emilie v Westby, Madison | 6-3,6-2 |
| ITF Women Stellenbosch | 2018/12/06 07:00 | Peer, Andrina v Westby, Madison | 6-4,1-6,1-6 |
| Arcadia, Singles Qualifying W-ITF-USA-07A | 2019/03/12 17:30 | Wilcox, Hailey v Gorchanyuk, Oleksandra | 6-3,6-7,11-9 |
| Arcadia, Singles Qualifying W-ITF-USA-07A | 2019/03/11 14:00 | Wilcox, Hailey v Stewart, Jane | 6-2,6-4 |
| ITF - W15 Fort-de-France | 2019/01/10 16:30 | Kennel, Karin v Wilcox, Hailey | 6-1,6-1 |
| ITF - W15 Fort-de-France | 2019/01/08 15:30 | Wilcox, Hailey v Rollin, Anais | 6-1,6-0 |
| ITF Women Bogota | 2018/12/05 18:30 | Wilcox, Hailey v Giraldo, Gabriela | 6-2,1-6,3-6 |
| ITF Women Bogota | 2018/12/03 14:30 | Vivian Mayumi Toma v Wilcox, Hailey | 1-6,1-6 |
| ITF Women Bogota | 2018/12/02 16:45 | Wilcox, Hailey v Gomez, Ana Maria | 6-1,6-2 |
| ITF Women Bogota | 2018/12/01 15:00 | Vargas Carrascal, Mariana v Wilcox, Hailey | 4-6,1-6 |