Alex de Minaur has battled back from an opening set loss to snatch victory from Vasek Pospisil at the Citi Open in Washington.
The 19-year-old rallied after dropping a hard-fought first set to defeat the world No.92 6-7 (8-6) 6-2 6-2, in a match lasting two hours and 23 minutes.
De Minaur broke serve four times as injury appeared to hamper the Canadian in the second set.
The world No.72 will now face Steve Johnson after the American received a bye in the first round.
Fellow Australian Alex Bolt was left trailing American Tommy Paul in his opening round of the tournament after the match was suspended due to rain.
The world No. 166 will have to claw his way back from a 3-6 7-6 (7-0) 1-4 score to defeat his lower-ranked opponent.
Earlier, James Duckworth scored a crucial win as he tries to claw his way back up the ATP rankings.
The Australian, who was once ranked 82 in the world, has slipped to No. 654 after a prolonged absence on tour due to foot, shoulder and elbow surgeries.
The 26-year-old Sydneysider beat local Thai-Son Kwiatkowski 6-3 7-5 to set up a second-round encounter with compatriot Nick Kyrgios.
Kyrgios is the tournament's No.5 seed and received a bye into the next round.
In a closely fought affair, Duckworth sent down 13 aces to Kwiatkowski's 12 and clinched the only two break points of the match.
Despite a gallant effort, Australian Jordan Thompson bowed out in the first round in a 6-4 7-6 (7-4) loss to Jared Donaldson.
Thompson, the world No.97, went toe-to-toe with his higher-ranked opponent (No.62) before succumbing in the second-set tiebreaker.
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