Stadium: Court 1 Round: 45 Ground: Hardcourt indoor
| ITF Women Rancho Santa Fe | 2018/02/21 20:30 | Ann Li v Louisa Chirico | 6-1,6-2 |
| ITF W25 Daytona Beach | 2019/01/17 15:30 | Anna Bondar v Ann Li | 6-4,6-4 |
| ITF W25 Daytona Beach | 2019/01/16 18:10 | Irene Burillo Escorihuela v Ann Li | 4-6,4-6 |
| WTA Houston | 2018/11/13 16:00 | Ann Li v Fanny Stollar | 5-7,3-6 |
| WTA Houston | 2018/11/11 17:30 | Sanaz Marand v Ann Li | 6-4,3-6,3-6 |
| WTA Houston | 2018/11/10 22:25 | Ana Veselinovic v Ann Li | 3-6,1-6 |
| ITF Women Las Vegas | 2018/11/04 21:45 | Ann Li v Julia Elbaba | 4-6,6-7 |
| ITF Women Tyler | 2018/10/31 15:00 | Ann Li v Kayla Day | 2-6,5-7 |
| ITF Women Tyler | 2018/10/30 15:00 | Ann Li v Gabriela Talaba | 6-2,6-4 |
| ITF W25 Plantation | 2019/01/25 15:00 | Hailey Baptiste v Louisa Chirico | 7-6,6-4 |
| ITF W25 Plantation | 2019/01/23 18:05 | Louisa Chirico v Catherine Harrison | 6-1,6-1 |
| ITF W25 Daytona Beach | 2019/01/18 15:30 | Francoise Abanda v Louisa Chirico | 6-2,6-7,6-1 |
| ITF W25 Daytona Beach | 2019/01/17 15:30 | Louisa Chirico v Daniela Seguel | 3-6,6-3,6-2 |
| ITF W25 Daytona Beach | 2019/01/16 16:10 | Louisa Chirico v Caty McNally | 0-6,6-4,6-4 |
| WTA Houston | 2018/11/12 22:00 | Reka-Luca Jani v Louisa Chirico | 6-2,6-3 |
| WTA Houston | 2018/11/11 16:00 | Kristina Kucova v Louisa Chirico | 7-6,6-4 |
| WTA Houston | 2018/11/10 16:40 | Louisa Chirico v Maria Mateas | 7-5,6-3 |