Hewitt kicks off his record 20th and final appearance at his home grand slam against another wildcard in 134th-ranked James Duckworth, only the second time he has faced an Australian at the tournament.
The last time was in 2003, when Hewitt was top seed and at the peak of his powers, and a straight-sets rout of local battler Todd Larkham in the second round was the result.
With his role as mentor to the nation's next generation now formalised as Davis Cup captain, Hewitt, now world number 306, will take on a player who was seeking grand slam tips from him just before the draw was announced.
"Always bound to happen, wasn't it?" the battle-worn 34-year-old remarked dryly to reporters on Saturday.
"Especially now that I've got a second hat on, a full-time job as Davis Cup captain.
"Yeah, it's awkward, but in another way it's fun to go out there with Ducks. I've been helping him the last few years.
"(We'll) see how good a student he is.
"Ducks was text messaging me yesterday morning before the draw was out.
"So, yeah, obviously I think both of us will look back on it. No matter what happens, it will be a satisfying enjoyment of going out there and playing against him."
The clash between Hewitt's roles also played out at the U.S. Open, where Bernard Tomic, his successor as Australia's number one, edged him in a five-set match in the second round.
"(That) was really tough," said the 2001 U.S. Open champion Hewitt, who also won Wimbledon in 2002.
"I hit with Bernie about three days before we played each other. He was asking me things to help his service and stuff like that. That was really awkward."
Although long and colourful, Hewitt's record at the Australian Open has not been a stand-out among the grand slams, though he did make the 2005 final won by Marat Safin.
Bowing out in front of home fans seems a fitting conclusion to a career that began in earnest at Melbourne Park in 1997, when a 15-year-old Hewitt became the youngest qualifier to make the main draw.
Nineteen years on, Hewitt said he was still battling the pre-grand slam nerves and trying not to think about the Duckworth match as possibly his last.
"I just try to go out there and put on a good show," he said.
"Hopefully the body holds up."
(Editing by Patrick Johnston)
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