Wednesday, Second Round
 Jelena Jankovic (SRB #12) vs. Alisa Kleybanova (RUS #363)
Head-to-head: Kleybanova leads 3-2
While Jelena Jankovic will be the on-paper favorite in her tilt with Alisa Kleybanova, the Russian will certainly be the sentimental favorite. Kleybanova survived a tight three-setter in the first round against Monica Puig in her first Grand Slam match since the 2011 Australian Open. The former Top 20 player did not play beyond May in 2011 because of Hodgkin's lymphoma, only played one event in 2012 and just played her first WTA events of 2013 this summer. If she is able to beat Jankovic, it would be her best win in terms of ranking since February 2011.
Though Kleybanova actually leads her series with Jankovic, they haven't played in over three years and Jankovic is in fine form these days. The Serb's impressive season has included her first WTA title in almost three years at Bogotá in February, a runner-up showing in Charleston and semifinal outings in Miami, Nürnberg and Cincinnati. Also, she had her best Grand Slam experience here, reaching the final in 2008.
Zheng Jie (CHN #56) vs. Venus Williams (USA #60)
Head-to-head: Williams leads 1-0
Venus Williams reminded the public that she is still capable of world-class tennis when she routed World No.14 Kirsten Flipkens, 61 62, in her opener on Monday. It was the best win for the seven-time Grand Slam and two-time US Open champ since she defeated then-World No.6 in Samantha Stosur in the quarterfinals of Cincinnati in August 2012.
As for second round foe Zheng Jie, Williams won their one previous encounter in straight sets, but that was nine and a half years ago in Miami. Since that time, Zheng has twice been a Grand Slam semifinalist - at Wimbledon in 2008 and at the Australian Open in 2010. She also reached a career-high ranking of No.15 in 2009. However, she didn't come into this year's US Open in the best form, having lost four matches in a row until her first round victory over Kiki Bertens.
Arthur Ashe Stadium
 Sloane Stephens (USA #16) vs. Urszula Radwanska (POL #38)
Head-to-head: Radwanska leads 1-0
It looked like Sloane Stephens' 2013 US Open campaign would be a short one when she trailed Mandy Minella 4-2 in the third set of their first round battle, but as she often does in Grand Slam play, Stephens found a way to win. That improved her record in majors this year to 13-3 compared to just 17-15 in other WTA events.
Urszula Radwanska was much more impressive in her first round, dropping just four games to Irina-Camelia Begu. On top of that, she won comfortably in her only previous clash with Stephens at Indian Wells earlier this year. Another triumph would give her six Top 20 wins this year and 13 for her career.