Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
| ITF W100 Midland | 2019/01/28 18:40 | Ann Li v Louisa Chirico | 7-6,6-2 |
| ITF Women Rancho Santa Fe | 2018/02/21 20:30 | Ann Li v Louisa Chirico | 6-1,6-2 |
| WTA Guadalajara | 2023/09/17 17:00 | Louisa Chirico v Jasmine Paolini | 0-6,6-7 |
| WTA San Diego | 2023/09/12 18:30 | Louisa Chirico v Danielle Rose Collins | 5-7,0-6 |
| WTA San Diego | 2023/09/10 18:00 | Renata Zarazua v Louisa Chirico | 3-6,6-3,4-6 |
| WTA San Diego | 2023/09/09 17:00 | Louisa Chirico v Caroline Dolehide | 7-6,6-2 |
| US Open Women | 2023/08/25 18:25 | Louisa Chirico v Olivia Gadecki | 7-6,3-6,4-6 |
| US Open Women | 2023/08/23 18:05 | Nao Hibino v Louisa Chirico | 6-7,3-6 |
| WTA Stanford | 2023/08/12 17:00 | Yafan Wang v Louisa Chirico | 7-5,6-1 |
| WTA Montreal | 2023/08/05 18:35 | Louisa Chirico v Kayla Day | 2-6,2-6 |
| ITF W60 Templeton | 2023/09/26 20:20 | Liv Hovde v Ann Li | 6-3,6-7,0-6 |
| WTA Guadalajara | 2023/09/18 01:25 | Sloane Stephens v Ann Li | 7-5,6-4 |
| WTA Guadalajara | 2023/09/15 16:00 | Ann Li v Jessica Failla | 6-1,6-1 |
| US Open Women | 2023/08/25 14:00 | Yafan Wang v Ann Li | 6-2,6-4 |
| US Open Women | 2023/08/23 23:10 | Ann Li v Carlota Martinez Cirez | 7-6,6-2 |
| WTA Cincinnati | 2023/08/16 23:00 | Ann Li v Aryna Sabalenka | 5-7,6-2,4-6 |
| WTA Cincinnati | 2023/08/15 20:25 | Magda Linette v Ann Li | 6-0,6-7,2-6 |
| WTA Cincinnati | 2023/08/13 14:00 | Ann Li v Alize Cornet | 6-3,6-3 |