By Ian Ransom
Simon, whose ranking peaked at six in 2009, beat Federer in three sets at the 2008 Toronto Masters and then repeated the feat a few months later in a round robin match at the Masters Cup in Shanghai as the Swiss struggled with a back injury.
Federer tends to remember his few losses far better than his long catalog of victories and had a sound recollection of his defeats to the Frenchman, who has been in solid form with victory at the Sydney International.
"Maybe I will look just a bit more into what has worked and what has not worked against him in the past," the world number two said after blitzing first-round opponent Lukas Lacko.
"He was on a great run there, playing the finals I think in Madrid, beating Rafa there. So he's beaten the best in the world really. If he can do it once, he always feels he can do it again, which he did against me."
Federer and Simon will meet on the Rod Laver Arena court in the evening session after Andy Roddick takes on Russia's Igor Kunitsyn.
Serbian Novak Djokovic, whose match against a Bosnian-born opponent at the 2009 tournament was the catalyst for a brawl between rival fans, will play Croatian Ivan Dodig at Hisense Arena.
"There's no reason (for fans) to create any kind of bad feeling about our countries," Djokovic said. "Hopefully nothing will happen."
In the women's draw, the spotlight turns on a pair of cautious comebacks, with Venus Williams taking on Czech Sandra Zahlavova as she continues her return after four months out with a knee injury.
Last year's finalist Justine Henin, out for six months with an elbow injury, plays Britain's Elena Baltacha first up on Rod Laver Arena.
Top seed Caroline Wozniacki is battling for respect as a number one without a grand slam, but will have to do it off center court against American Vania King at the Hisense Arena.
(Editing by Pritha Sarkar)
Receive your weekly recap of all the happenings around the world of sports.