Stadium: Court 5 Round: 45 Ground: Hardcourt outdoor
| 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 |
| ITF Women Mexico City | 2018/10/29 16:30 | Mar, Tricia v Wilcox, Hailey | 3-6,7-5,3-6 |
| ITF Women Tacarigua | 2018/05/07 14:00 | Wilcox, Hailey v Leduc, Catherine | 2-6,1-6 |
| ITF Women Monastir | 2018/11/11 09:00 | Stewart, Jane v Aubuchon, Micheline | 0-6,6-4,4-6 |
| ITF Women Monastir | 2018/11/07 11:55 | Stewart, Jane v Eklund, Mia | 2-6,1-6 |
| ITF Women Monastir | 2018/10/29 11:00 | Peddi Reddy, Sri Vaishnavi v Stewart, Jane | 6-4,6-4 |
| ITF Women Monastir | 2018/10/22 08:30 | Genovese, Elaine v Stewart, Jane | 6-0,6-2 |
| ITF Women Monastir | 2018/10/21 08:30 | Stewart, Jane v Peckl, Kerstin | 6-0,6-3 |
| ITF Women Monastir | 2018/10/16 08:30 | Prati, Federica v Stewart, Jane | 6-4,6-0 |
| ITF Women Monastir | 2018/10/15 08:30 | Stewart, Jane v Angelina Graovac | 3-6,6-4,6-3 |
| ITF Women Monastir | 2018/10/08 08:30 | Stewart, Jane v Emmanuelle Girard | 1-6,1-6 |