Madison Keys 6-1,6-7,6-3 Venus Williams 2016-07-28 22:30
Round: 26 Ground: Hardcourt outdoor
Home History
| WTA Montreal | 2016/07/27 21:15 | Madison Keys v Madison Brengle | 6-4,6-3 |
| WTA Montreal | 2016/07/26 18:45 | Madison Keys v Elena Vesnina | 6-4,6-0 |
| Wimbledon Women | 2016/07/04 12:00 | Simona Halep v Madison Keys | 6-7,6-4,6-3 |
| Wimbledon Women | 2016/07/02 16:15 | Alize Cornet v Madison Keys | 4-6,7-5,2-6 |
| Wimbledon Women | 2016/06/30 10:50 | Kirsten Flipkens v Madison Keys | 4-6,6-4,3-6 |
| Wimbledon Women | 2016/06/27 12:55 | Laura Siegemund v Madison Keys | 3-6,1-6 |
| Billie Jean King Cup | 2016/04/16 01:00 | Daria Saville v Madison Keys | 4-6,2-6 |
| Wimbledon Women | 2015/07/07 15:10 | Madison Keys v Agnieszka Radwanska | 6-7,6-3,3-6 |
Away History
| WTA Montreal | 2016/07/27 18:30 | Barbora Strycova v Venus Williams | 3-6,0-6 |
| Wimbledon Women | 2016/07/07 13:15 | Angelique Kerber v Venus Williams | 6-4,6-4 |
| Wimbledon Women | 2016/07/05 12:00 | Venus Williams v Yaroslava Shvedova | 7-6,6-2 |
| Wimbledon Women | 2016/07/04 14:15 | Venus Williams v Carla Suarez Navarro | 7-6,6-4 |
| Wimbledon Women | 2016/07/01 12:00 | Venus Williams v Daria Kasatkina | 7-5,4-6,10-8 |
| Wimbledon Women | 2016/06/30 11:30 | Venus Williams v Maria Sakkari | 7-5,4-6,6-3 |
| Wimbledon Women | 2016/06/27 12:00 | Venus Williams v Donna Vekic | 7-6,6-4 |
| Challenger Kaohsiung | 2016/02/14 06:00 | Venus Williams v Misaki Doi | 6-4,6-2 |