The 16-year-old son of Australian great Lleyton Hewitt suffered a 7-6 (11-9) 6-1 loss to American Brandon Holt on Sunday.
Ranked No.198 in the world, Holt also has famous tennis pedigree, with his mother being former women's world No.1 Tracy Austin.Â
Holt displayed true grit to fight back from 5-2 in the opening set before saving two set points to snatch the seesawing tiebreaker.
Hewitt was unable to recover and will now turn his attention to trying to qualify for the Australian Open starting on January 12.
Twenty-eight years after his father successfully qualified at age 15, Hewitt has been handed a wildcard into the Melbourne Park qualies.
Already toweing over his dad and possessing impressive serving firepower, Hewitt will also contest the Australian Open boys' singles after crashing out in the first round this year.
The teenager is currently the junior world No.107, but reached as high as No.99 in October and was a nominee for Australian junior male of the year at this month's Newcombe Medal awards ceremony.
Holt, meanwhile, will play Canadian Alexis Galarneau next for a place in the Canberra main draw.