[91] Venus Williams 2-6,4-6 Brady, Jennifer [14] 2021-04-30 16:10
Stadium: Manolo Santana Stadium Round: 24 Ground: Clay
Home History
| WTA - Miami | 2021/03/23 18:20 | Zarina Diyas v Venus Williams | 6-2,7-6 |
| Open d'Australie - Femmes | 2021/02/10 05:20 | Venus Williams v Sara Errani | 1-6,0-6 |
| Open d'Australie - Femmes | 2021/02/08 00:00 | Flipkens, Kirsten v Venus Williams | 5-7,2-6 |
| WTA Yarra Valley Classic | 2021/02/02 09:05 | Venus Williams v Kvitova, Petra | 6-7,5-7 |
| WTA Yarra Valley Classic | 2021/01/31 06:55 | Arantxa Rus v Venus Williams | 1-6,3-6 |
| Open de France - Femmes | 2020/09/27 12:00 | Anna Karolina Schmiedlova v Venus Williams | 6-4,6-4 |
| WTA - Rome | 2020/09/16 12:25 | Victoria Azarenka v Venus Williams | 7-6,6-2 |
| US Open Women | 2020/09/01 23:00 | Muchova, Karolina v Venus Williams | 6-3,7-5 |
Away History
| WTA - Stuttgart | 2021/04/20 17:25 | Brady, Jennifer v Kvitova, Petra | 4-6,3-6 |
| WTA - Miami | 2021/03/26 23:00 | Brady, Jennifer v Sara Sorribes Tormo | 6-3,4-6,1-6 |
| WTA - Doha | 2021/03/01 11:30 | Brady, Jennifer v Kontaveit, Anett | 1-6,2-6 |
| Open d'Australie - Femmes | 2021/02/20 08:30 | Brady, Jennifer v Naomi Osaka | 4-6,3-6 |
| Open d'Australie - Femmes | 2021/02/18 04:40 | Muchova, Karolina v Brady, Jennifer | 4-6,6-3,4-6 |
| Open d'Australie - Femmes | 2021/02/17 02:20 | Brady, Jennifer v Jessica Pegula | 4-6,6-2,6-1 |
| Open d'Australie - Femmes | 2021/02/15 02:15 | Donna Vekic v Brady, Jennifer | 1-6,5-7 |
| Open d'Australie - Femmes | 2021/02/13 02:30 | Brady, Jennifer v Kaja Juvan | 6-1,6-3 |