Head to Head
| ITF W80 Charlottesville | 2019/04/28 16:00 | Whitney Osuigwe v Madison Brengle | 6-4,1-6,6-3 |
Home History
| WTA Indian Wells | 2020/03/03 20:20 | Yanina Wickmayer v Madison Brengle | 6-7,7-6,6-2 |
| ITF W100 Nicholasville | 2020/02/15 17:55 | Madison Brengle v Olga Govortsova | 4-6,3-6 |
| ITF W100 Nicholasville | 2020/02/14 15:50 | Yanina Wickmayer v Madison Brengle | 2-6,6-4,1-6 |
| ITF W100 Nicholasville | 2020/02/13 18:55 | Hanna Chang v Madison Brengle | 4-6,4-6 |
| ITF W100 Midland | 2020/02/06 01:15 | Madison Brengle v Gabriela Talaba | 2-6,6-7 |
| WTA Newport Beach | 2020/02/02 18:00 | Madison Brengle v Stefanie Voegele | 6-1,3-6,6-2 |
| WTA Newport Beach | 2020/02/01 18:00 | Madison Brengle v Nadia Podoroska | 6-4,7-6 |
| WTA Newport Beach | 2020/01/31 19:00 | Jessica Pegula v Madison Brengle | 6-1,6-7,2-6 |
Away History
| Matchplay 120 Women | 2020/06/12 19:00 | Jamie Loeb v Whitney Osuigwe | 4-6,3-6 |
| Matchplay 120 Women | 2020/06/09 18:00 | Caroline Dolehide v Whitney Osuigwe | 6-4,6-4 |
| US Pro Tennis Series Women | 2020/05/23 14:45 | Seone Mendez v Whitney Osuigwe | 7-5,5-7,6-10 |
| US Pro Tennis Series Women | 2020/05/21 19:05 | Whitney Osuigwe v Luisa Stefani | 2-6,6-3,7-10 |
| US Pro Tennis Series Women | 2020/05/20 21:10 | Whitney Osuigwe v Gabriela Talaba | 6-7,4-6 |
| ITF W100 Nicholasville | 2020/02/13 19:50 | Whitney Osuigwe v Yanina Wickmayer | 3-6,4-6 |
| ITF W100 Nicholasville | 2020/02/11 20:40 | Whitney Osuigwe v Aldila Sutjiadi | 6-3,6-3 |
| Australian Open Women | 2020/01/14 06:00 | Martina Di Giuseppe v Whitney Osuigwe | 3-6,6-4,6-1 |