| WTA Cincinnati | 08/16 23:00 | 27 | [65] Venus Williams v Madison Keys [18] | 2-6,3-6 | |
| WTA Cincinnati | 08/15 23:00 | 26 | [18] Madison Keys v Simona Halep [4] | 6-1,3-6,7-5 | |
| WTA Cincinnati | 08/14 20:05 | 25 | [18] Madison Keys v Daria Kasatkina [41] | 6-4,6-1 | |
| WTA Cincinnati | 08/13 18:15 | 24 | [18] Madison Keys v Garbine Muguruza [27] | 6-7,7-6,6-4 | |
| WTA Toronto | 08/06 21:30 | 24 | [17] Madison Keys v Donna Vekic [24] | 6-3,6-7,6-7 | |
| WTA Washington | 07/30 22:15 | 25 | [283] Hailey Baptiste v Madison Keys [17] | 7-6,6-2 | |
| Wimbledon - Kobiety | 07/03 18:20 | 24 | [16] Madison Keys v Polona Hercog [60] | 2-6,4-6 | |
| Wimbledon - Kobiety | 07/01 10:00 | 23 | [16] Madison Keys v Luksika Kumkhum [107] | 6-3,6-2 | |
| French Open - Kobiety | 06/06 10:00 | 27 | [14] Madison Keys v Ashleigh Barty [8] | 3-6,5-7 | |
| French Open - Kobiety | 06/03 09:00 | 26 | [42] Katerina Siniakova v Madison Keys [14] | 2-6,4-6 | |
| French Open - Kobiety | 06/01 12:25 | 25 | [117] Anna Blinkova v Madison Keys [14] | 3-6,7-6,4-6 | |
| French Open - Kobiety | 05/30 17:25 | 24 | [132] Priscilla Hon v Madison Keys [14] | 5-7,7-5,3-6 | |
| French Open - Kobiety | 05/28 15:15 | 23 | [70] Evgeniya Rodina v Madison Keys [14] | 1-6,2-6 | |
| WTA Rzym | 05/16 10:50 | 25 | [14] Madison Keys v Sofia Kenin [37] | 7-6,3-6,4-6 | |
| WTA Rzym | 05/13 16:00 | 24 | [14] Madison Keys v Polona Hercog [71] | 6-4,7-6 | |
| WTA Madryt | 05/05 10:50 | 24 | [14] Madison Keys v Sorana Cirstea [93] | 6-3,4-6,1-6 | |
| World Group Play Offs | 04/21 20:35 | - | Madison Keys v Timea Bacsinszky | Cancelled | |
| 2019 Fed Cup | 04/20 19:30 | - | [14] Madison Keys v Viktorija Golubic [80] | 2-6,3-6 | |
| WTA Charleston | 04/07 17:00 | 29 | [18] Madison Keys v Caroline Wozniacki [13] | 7-6,6-3 | |
| WTA Charleston | 04/06 18:40 | 28 | [18] Madison Keys v Monica Puig [63] | 6-4,6-0 | |
| WTA Charleston | 04/05 20:30 | 27 | [8] Sloane Stephens v Madison Keys [18] | 6-7,6-4,2-6 | |
| WTA Charleston | 04/04 21:50 | 26 | [31] Jelena Ostapenko v Madison Keys [18] | 5-7,2-6 | |
| WTA Charleston | 04/03 23:00 | 25 | [59] Tatjana Maria v Madison Keys [18] | 6-7,6-4,4-6 | |
| WTA Miami | 03/21 23:30 | 24 | [83] Samantha Stosur v Madison Keys [16] | 6-4,4-6,6-4 | |
| WTA Indian Wells | 03/09 20:20 | 24 | [17] Madison Keys v Mona Barthel [97] | 6-3,1-6,5-7 | |
| 2019 Fed Cup | 02/10 18:00 | 27 | [17] Madison Keys v Ashleigh Barty [13] | 4-6,1-6 | |
| 2019 Fed Cup | 02/09 19:40 | 27 | [17] Madison Keys v Kimberly Birrell [157] | 6-2,6-2 | |
| Australian Open - Kobiety | 01/21 00:00 | 26 | [17] Madison Keys v Elina Svitolina [7] | 2-6,6-1,1-6 | |
| Australian Open - Kobiety | 01/19 04:45 | 25 | [14] Elise Mertens v Madison Keys [17] | 3-6,2-6 | |
| Australian Open - Kobiety | 01/17 02:00 | 24 | [89] Anastasia Potapova v Madison Keys [17] | 3-6,4-6 |
Wikipedia - Madison Keys
Madison Keys (ur. 17 lutego 1995 w Rock Island) – amerykańska tenisistka, finalistka US Open 2017 w grze pojedynczej. Status profesjonalny uzyskała w styczniu 2009 roku. Jest zawodniczką praworęczną z oburęcznym backhandem.