Sixteen women will start the day on manic Monday and only eight will move on to the quarterfinals. The tournament begins in earnest on Monday for these sixteen remaining players, which eight women will capture a coveted quarterfinal spot at the end of the day?
 Angelique Kerber vs.  Garbine Muguruza: Muguruza leads their head-to-head 4:3 and she won their last four encounters. Will she make it five in a row?
 Simona Halep vs. Victoria Azarenka: Azarenka leads their head-to-head 2:1; however, she just returned from maternity leave. Halep has the burden of expectations on her shoulder; will that continue to impact her play?
 Elina Svitolina vs.  Jelena Ostapenko will be their first meeting and the recently crowned French Open Champion will have her hands full against the fiery Ukrainian.
 Caroline Wozniacki vs.  Coco Vandeweghe: both previous meetings have gone to the Dane; however, Vandeweghe did manage to win a set the last time they played. Perhaps if she watched Anett Kontaveit’s match from Saturday, she will take comfort in knowing she can overpower her opponent. Poor mobility around the court may be the weakest link in her game and Wozniacki will look to capitalize on that.
 Johanna Konta vs.  Caroline Garcia: Konta has been slated as the favorite to win this tournament with the departure of Petra Kvitova and Karolina Pliskova. She will have to get by Garcia though. The Frenchwoman beat her in their last encounter and they are tied up at 2:2.
 Svetlana Kuznetsova vs.  Agnieszka Radwanska: the Russian, Kuznetsova, leads this head-to-head 13:4 and she has won the last three encounters; however, they are tied 1:1 on grass.
 Venus Williams vs.  Ana Konjuh will be their first meeting. The five-time Wimbledon Champion, Williams, will have her hands full against the crafty play of this young Croatian. Konjuh knows how to play on grass as well, with her only title coming on the surface in 2015.
Petra Martic vs. Magdalena Rybarikova will be another first meeting. The Slovakian has four titles to her name in comparison to none for Martic. One of those titles was on grass, so she knows how to play on this surface. Both players are hoping to go one step further than their previous best of the third round at Wimbledon.
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