Head to Head
| ITF W60 Honolulu | 2019/07/12 22:50 | Whitney Osuigwe v Jamie Loeb | 4-6,6-4,1-6 |
| ITF Women Stockton | 2018/10/04 20:00 | Jamie Loeb v Whitney Osuigwe | 3-6,1-6 |
Home History
| Matchplay 120 Women | 2020/06/10 14:00 | Caroline Dolehide v Jamie Loeb | 4-6,6-2,6-4 |
| Matchplay 120 Women | 2020/06/08 18:00 | Jennifer Brady v Jamie Loeb | 5-7,7-5,3-6 |
| Matchplay 120 Women | 2020/06/05 16:00 | Jamie Loeb v Caroline Dolehide | 6-4,1-6,7-5 |
| Matchplay 120 Women | 2020/06/03 14:00 | Jamie Loeb v Jennifer Brady | 2-6,1-6 |
| Matchplay 120 Women | 2020/06/01 13:13 | Jamie Loeb v Caroline Dolehide | 5-7,0-0 |
| Matchplay 120 Women | 2020/05/29 13:00 | Jamie Loeb v Laura Siegemund | 6-1,5-7,1-6 |
| US Pro Tennis Series Women | 2020/05/10 16:45 | Jamie Loeb v Jessica Livianu | 3-0 |
| US Pro Tennis Series Women | 2020/05/10 14:00 | Jamie Loeb v Luisa Stefani | 4-6,5-7 |
Away History
| 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 |
| WTA Brisbane | 2020/01/04 01:00 | Lizette Cabrera v Whitney Osuigwe | 6-2,6-1 |