The British tennis player beat home favourite Louisa Chirico in the round of 32 by a score of 6-4, 6-2.
Halep played against Spanish player Cristina Bucsa in the round of 32 of the competition on Monday and recorded a comfortable 6-3, 7-5 victory.
Nick Kyrgios recorded a 6-3, 6-2 win over Marcos Giron on Tuesday in a match where he hit 12 aces.
The Aussie defeated the likes of Filip Krajinovic and Stefanos Tsitsipas en route to his best ever result at Wimbledon.
The Scot had taken part in the 2022 Hall of Fame Open last month where he was seeded sixth and reached the quarter-final.
The competition is a part of the US Open Series leading up to the US Open grand slam in September, the WTA 250 of the 2022 WTA Tour, and the ATP Tour 500 series.
Jannik Sinner beat Mackie McDonald 7-5, 4-6, 7-5 to take the Citi Open title on Sunday in a three-hour long final encounter.
Rafael Nadal beat Jack Sock 6-2, 4-6, 7-6(1) in a Citi Open match on Thursday, nearly two months after he last played a competitive game.