Bolt and Popyrin’s exceptional wins gave Australia its best start to the Open in 15 years.
Ranked 159 at the start of the year, Bolt incredibly saved four match points against the former world number six Gilles Simon in a five-set classic - 2-6, 6-4, 4-6, 7-6 (10), 6-4 in just over four hours.
Bolt, 26, was ranked outside the top 500 just three years ago and now finds himself in the Australian Open last 32.
“This is the best thing I have ever experienced in my life,” Bolt said post-match at the Australian Open. “It is unbelievable to have everyone behind me tonight. They really got me over the line.
“I think we are in a pretty good spot. Hopefully, some of us can win another round and go deeper into the tournament.”
Fresh after Aussie hopefuls Nick Kyrgios and Bernard Tomic’s first-round straight-sets exits, unheralded Bolt showed the tenacity and fight required to come from behind and stun his highly-fancied opponent.
Earlier, fellow wildcard Popyrin also claimed the biggest win of his career against seventh seed, and French Open runner-up, Dominic Thiem.
The 19-year-old ranked 149 in the world, dominated Thiem for the majority of the contest before the Austrian retired trailing 5-7, 4-6, 0-2.
The world number eight was frustrated by the Aussie hard-hitting, with Thiem destroying a racket during the first set.
“It's never easy winning like this, but I just want to thank everyone that came out and supported me today. It's an unbelievable feeling," Popyrin said.
Bolt and Popyrin join 27th seed Alex de Minaur as the Aussies through to the third round on the men’s side, while Ash Barty and Kimberly Birrell are still alive in the women’s singles.
It’s the first time since 2003 that Australia has five players in the third round.
Could this trio of Alex's be the nucleus of our next Australian tennis stars?
Time will tell. But for now, they are all showing promising signs which indicate the future of Australian tennis is bright.
Next up though, de Minaur, Bolt and Birrell have arguably the toughest assignments.
De Minaur, 19, meets 17-time grand slam champion Rafael Nadal, Bolt faces fourth seed Alexander Zverev and 240th-ranked 20-year-old Birrell plays world number 2 Angelique Kerber.
Off the back of his upset victory over Thiem, Popyrin will somewhat fancy his chances against 28th seeded Frenchman Lucas Pouille.
And Barty, 22, faces 41st ranked Maria Sakkari, before a potential fourth-round showdown with either Caroline Wozniacki or Maria Sharapova.
