The former Australia defender led Western Sydney Wanderers to the decider three times in their first four seasons but was defeated in all of them, the last time a 3-1 reverse against Adelaide United in 2016.
After a brief, ill-fated coaching stint in Turkish football, Popovic returned to the A-League last year and has transformed the Glory in his first year in charge.
Having missed the playoffs last year under sacked former boss Kenny Lowe, the Glory claimed the Premier's Plate last month as the top team in the regular season
That was the club's first silverware since the A-League was re-born out of the ashes of the National Soccer League -- a competition they won in its last two seasons.
Their turnaround has been built on a foundation of smart recruiting, with a host of internationals following the highly regarded Popovic to Australia's most remote major city.
Socceroos Matthew Spiranovic, Jason Davidson and Chris Ikonomidis were among the fresh blood, and the latter two players made the Professional Footballers Australia team of the year.
It could have all been very different, however, as the Glory all but squandered their place in Sunday's decider during a nerve-jangling semi-final win over at Adelaide United last week.
They have colourful goalkeeper Liam Reddy to thank for rescuing them with four saves after they gave up a 2-0 lead in a match that went to a penalty shootout.
The veteran, who was once punished for getting drunk on a flight to an A-League playoff, has had a tense relationship with previous coaches but said Popovic had been the ultimate player manager.
"He is the most professional coach I’ve had in terms of how he wants things done and what he expects of himself and his staff, but also his players," the 37-year-old told local media this week.
Popovic will match wits against an old friend in the Sky Blues boss Steve Corica, who has also had a stellar season in his first season as head coach.
The two were team mates at Sydney and also in Japan during their playing days.
"Come Sunday the competitiveness will come out, but I’m delighted for him, and I know he is for me," Popovic said.
In contrast to the Glory, three-times champion Sydney stormed into the Grand Final for the third time in five years with a 6-1 humiliation of champions Melbourne Victory.
They will bid to match the Victory's record of four titles, having raised the A-League's distinctive championship trophy -- dubbed the "toilet seat" for its unusual design -- in 2006, 2010 and 2017.
Beating the Glory after a long flight to Perth will be tough but Sydney have the pedigree.
"They've been there before, they've got the experience, it's going to be no different," said Corica.
(Reporting by Ian Ransom; Editing by Nick Mulvenney)