Head to Head
| Matchplay 120 - Femenino | 2020/06/30 17:00 | Ann Li v Whitney Osuigwe | 3-6,2-6 |
| ITF W100 Bonita Springs | 2019/05/11 17:55 | Ann Li v Whitney Osuigwe | 0-6,7-5,6-4 |
| ITF Evansville - Femenino | 2017/07/27 20:10 | Ann Li v Whitney Osuigwe | 7-6,6-1 |
Home History
| Matchplay 120 - Femenino | 2020/06/30 17:00 | Ann Li v Whitney Osuigwe | 3-6,2-6 |
| WTA Indian Wells | 2020/03/02 21:00 | Ann Li v Harriet Dart | 1-6,7-6,1-6 |
| Open de Australia - Femenino | 2020/01/22 00:00 | Ann Li v Sofia Kenin | 1-6,3-6 |
| Open de Australia - Femenino | 2020/01/20 01:40 | Ann Li v Lizette Cabrera | 7-6,7-6 |
| Open de Australia - Femenino | 2020/01/17 02:30 | Ana Bogdan v Ann Li | 7-5,6-7,2-6 |
| Open de Australia - Femenino | 2020/01/16 04:10 | Yanina Wickmayer v Ann Li | 3-6,2-6 |
| Open de Australia - Femenino | 2020/01/14 06:05 | Maiar S A Abdelaziz v Ann Li | 3-6,5-7 |
| WTA Auckland | 2020/01/07 05:05 | Christina McHale v Ann Li | 7-5,6-2 |
Away History
| Matchplay 120 - Femenino | 2020/07/08 15:30 | Grace Min v Whitney Osuigwe | 6-3,1-6,1-6 |
| Matchplay 120 - Femenino | 2020/06/30 17:00 | Ann Li v Whitney Osuigwe | 3-6,2-6 |
| Matchplay 120 - Femenino | 2020/06/17 20:00 | Madison Brengle v Whitney Osuigwe | 6-2,7-6 |
| Matchplay 120 - Femenino | 2020/06/12 19:00 | Jamie Loeb v Whitney Osuigwe | 4-6,3-6 |
| Matchplay 120 - Femenino | 2020/06/09 18:00 | Caroline Dolehide v Whitney Osuigwe | 6-4,6-4 |
| EE.UU. - Pro Tennis Series - Femenino | 2020/05/23 14:45 | Seone Mendez v Whitney Osuigwe | 7-5,5-7,6-10 |
| EE.UU. - Pro Tennis Series - Femenino | 2020/05/21 19:05 | Whitney Osuigwe v Luisa Stefani | 2-6,6-3,7-10 |
| EE.UU. - Pro Tennis Series - Femenino | 2020/05/20 21:10 | Whitney Osuigwe v Gabriela Talaba | 6-7,4-6 |