Second seed Somdev Devvarman and qualifier Yuki Bhambri advanced to the second round of the $50,000 ATP Challenger event with contrasting wins in Charlottesville.
The 34-year-old American is only the sixth player since men's tennis turned professional in 1968 to achieve the feat.
Somdev Devvarman qualified for the ATP LA Open with a straight set win over American Alex Bogomolov Jr. but it was all over for Prakash Amritraj, who stumbled at the final hurdle. Second seed Somdev battled for one hour and 38 minutes to score a 7-5, 6-2 win over his sixth seed rival in the third and final qualifying round.
Top three seeds Roger Federer, Novak Djokovic and Andy Murray moved into the third round of the Cincinnati Open with relatively comfortable straight set victories on Wednesday.
Indian Davis Cupper Somdev Devvarman squandered a set lead en route to a first-round loss in the ATP Challenger Series' tournament in Calabasas, US. He went down 6-4, 4-6, 3-6 to local favourite Alex Bogomolov.