| WTA Courmayeur | 10/28 17:40 | 26 | [102] Magdalena Frech v Ann Li [48] | 7-5,3-6,1-6 | |
| WTA Courmayeur | 10/27 11:40 | 25 | [118] Kamilla Rakhimova v Ann Li [48] | 6-4,3-6,4-6 | |
| WTA Courmayeur | 10/25 08:00 | 25 | Xinyu Wang v Ann Li | Cancelled | |
| WTA Tenerife | 10/24 15:00 | 29 | [63] Maria Camila Osorio Serrano v Ann Li [60] | 1-6,4-6 | |
| WTA Tenerife | 10/23 14:00 | 28 | [60] Ann Li v Alize Cornet [66] | 6-2,6-1 | |
| WTA Tenerife | 10/22 11:25 | 27 | [56] Irina-Camelia Begu v Ann Li [60] | 5-7,5-7 | |
| WTA Tenerife | 10/20 12:55 | 26 | [60] Ann Li v Varvara Gracheva [80] | 6-4,6-2 | |
| WTA Tenerife | 10/18 11:45 | 25 | [65] Nuria Parrizas-Diaz v Ann Li [60] | 6-2,4-6,1-6 | |
| WTA - Indian Wells | 10/06 18:00 | 23 | [69] Ann Li v Doi, Misaki [109] | 2-6,7-5,5-7 | |
| WTA Chicago | 09/28 18:55 | 25 | [71] Ann Li v Muguruza, Garbine [9] | 4-6,4-6 | |
| WTA Chicago | 09/27 14:00 | 24 | [99] Donna Vekic v Ann Li [71] | 3-6,1-6 | |
| WTA Columbus | 09/24 19:15 | 27 | [73] Ann Li v Vandeweghe, Coco [153] | 4-6,4-6 | |
| WTA Columbus | 09/22 15:30 | 26 | [73] Ann Li v Harriet Dart [144] | 7-6,6-3 | |
| WTA Columbus | 09/20 19:45 | 25 | [73] Ann Li v Lizette Cabrera [162] | 6-2,6-2 | |
| US Open Women | 08/30 15:00 | 23 | [69] Ann Li v Kucova, Kristina [111] | 5-7,1-6 | |
| WTA Chicago | 08/23 16:00 | 25 | [67] Ann Li v Alize Cornet [68] | 7-6,0-6,4-6 | |
| WTA Chicago | 08/21 16:00 | 28 | [66] Ann Li v Clara Tauson [101] | 6-7,1-6 | |
| WTA Chicago | 08/20 16:00 | 27 | [112] Diyas, Zarina v Ann Li [66] | 4-6,6-2,3-6 | |
| WTA Chicago | 08/18 22:30 | 26 | [109] Oceane Dodin v Ann Li [69] | 3-6,1-6 | |
| WTA Chicago | 08/16 22:15 | 25 | [240] Whitney Osuigwe v Ann Li [69] | 3-6,4-6 | |
| WTA Montreal | 08/08 17:00 | 19 | [69] Ann Li v Oceane Dodin [106] | 1-6,4-6 | |
| WTA Montreal | 08/07 18:45 | 14 | Ann Li v Kupres, Mia | 6-1,6-3 | |
| Wimbledon Women | 06/29 10:00 | 23 | [72] Ann Li v Nadia Podoroska [39] | 4-6,6-7 | |
| WTA Bad Homburg | 06/23 17:05 | 26 | [12] Kvitova, Petra v Ann Li [70] | 6-2,6-7,6-1 | |
| WTA Bad Homburg | 06/21 11:30 | 25 | [399] Zaja, Anna v Ann Li [70] | 0-6,4-6 | |
| WTA Berlin | 06/12 11:20 | 14 | [75] Ann Li v Jule Niemeier [170] | 3-6,6-7 | |
| French Open Women | 06/03 09:00 | 24 | [75] Ann Li v Elina Svitolina [6] | 0-6,4-6 | |
| French Open Women | 06/01 09:00 | 23 | [75] Ann Li v Gasparyan, Margarita [100] | 6-0,6-1 | |
| WTA Monterrey | 03/20 21:00 | 28 | [72] Ann Li v Viktorija Golubic [102] | 2-6,4-6 | |
| WTA Monterrey | 03/19 19:00 | 27 | [72] Ann Li v Saisai Zheng [52] | 7-5,6-1 |