Head to Head
| WTA Charleston | 2023/04/02 15:35 | Ann Li v Kayla Day | 2-6,4-6 |
| ITF Women Tyler | 2018/10/31 15:00 | Ann Li v Kayla Day | 2-6,5-7 |
Home History
| ITF W100 Bonita Springs | 2023/05/06 15:25 | Astra Sharma v Ann Li | 2-6,3-6 |
| ITF W100 Bonita Springs | 2023/05/05 14:25 | Ann Li v Sachia Vickery | 7-5,2-6,6-1 |
| ITF W100 Bonita Springs | 2023/05/04 14:30 | Ann Li v Jamie Loeb | 6-4,7-5 |
| ITF W100 Bonita Springs | 2023/05/03 14:30 | Ashlyn Krueger v Ann Li | 3-6,5-7 |
| ITF W60 Charlottesville | 2023/04/27 16:40 | Diana Shnaider v Ann Li | 4-6,6-4,6-3 |
| ITF W60 Charlottesville | 2023/04/25 19:00 | Robin Anderson v Ann Li | 3-6,0-6 |
| ITF W100 Charleston | 2023/04/19 16:35 | Ann Li v Madison Brengle | 5-7,6-1,3-6 |
| ITF W25 Boca Raton | 2023/04/14 13:00 | Yulia Starodubtsewa v Ann Li | 7-5,2-6,6-2 |
Away History
| ITF W100 Bonita Springs | 2023/05/06 16:55 | Caroline Dolehide v Kayla Day | 6-7,6-1,0-6 |
| ITF W100 Bonita Springs | 2023/05/05 17:40 | Kayla Day v Marcela Zacarias | 7-5,6-3 |
| ITF W100 Bonita Springs | 2023/05/04 17:45 | Kayla Day v Katarzyna Kawa | 6-2,6-2 |
| ITF W100 Bonita Springs | 2023/05/03 17:05 | Kayla Day v Emma Bardet | 6-2,6-1 |
| ITF W60 Charlottesville | 2023/04/28 19:30 | Kayla Day v Emma Navarro | 3-6,1-6 |
| ITF W60 Charlottesville | 2023/04/27 13:55 | Kayla Day v Allie Kiick | 6-1,6-1 |
| ITF W60 Charlottesville | 2023/04/26 16:25 | Kayla Day v Makenna Jones | 6-2,6-2 |
| ITF W100 Charleston | 2023/04/20 16:40 | Nao Hibino v Kayla Day | 6-1,6-2 |