New York: Five-time champion Serena Williams will be facing 2006 winner Maria Sharapova in the first round of the 2019 US Open. This though the 22nd time that the two former world number ones will clash, it is the first time ever they will do so at the US Open. Serena has been chasing a 24th Grand Slam title and a first since her victory at the 2017 Australian Open after which she had taken a lengthy break from the game to give birth to her daughter. Sharapova has only managed to beat Serena twice. Defending champion Naomi Osaka, who beat Serena in the final in 2018, starts against Russian Anna Blinkova while Wimbledon winner Simona Halep and Petra Kvitova both play qualifiers.