In 2009, as a teenager, he robbed the Mosgiel Mini Mart of $350 while armed with a machete and was jailed for three years and four months.
Thirteen years later, McFarlane, 32, appeared in the Dunedin District Court yesterday after pleading guilty to another aggravated robbery - of the same dairy.
This time he was jailed for four years and 11 months.
McFarlane was driven to the Gordon Rd premises by Australian deportee Corey James Young, 31, on 3 March.
The shopkeeper was preparing to close when McFarlane walked in wielding a claw hammer.
Court documents described how the defendant had disguised himself by wearing a bandanna over his face, a hood over his head and gloves.
When the victim saw him raise the hammer over his head, he immediately backed off, but his retreat was not fast enough to evade the blow which fractured his skull.
While he fled to the rear of the store, locking a door behind him, McFarlane swiped 84 packets of tobacco and cigarettes, worth $3455, which he crammed inside a backpack.
He ran around the corner to King St where Young was waiting, threw the loot into the boot and jumped into the passenger seat.
Members of the public witnessed the hasty getaway and took note of the vehicle's registration plate.
Young drove off "well in excess" of the 50km/h limit towards the intersection with Gordon Rd, and sped through a red light.
He pleaded guilty to dangerous driving and robbery, and was sentenced to three years and two months' imprisonment.
The dairy owner, who spent five days in hospital, had since sold the business for half of what he paid for it, Judge Michael Turner said.
"The sale was driven by the fear there would be further robberies and his life would be at risk," he said.
The victim had moved cities but still suffered nightmares of being attacked.
A report identified McFarlane's alcohol and drug problems, but said those were secondary to his ongoing mental-health issues.
His childhood was plagued by trauma, which included exposure to violence and drugs, the court heard.
Counsel Sarah Saunderson-Warner also highlighted the fact her client had been involved in a vehicle crash a year ago in which he broke his neck.
Crown prosecutor Craig Power said Young returned to New Zealand from Australia - where had lived since the age of 13 - and had "little or no support" here, which made him a high risk of reoffending.
He had two children living across the Tasman.
Like McFarlane, Young, too, had suffered a head injury - his from a horse-riding incident 11 years ago.
Young blamed his offending, which included driving convictions from an earlier incident in the Octagon, on a lack of support on his return to the country.
Both defendants were ordered to repay the cost of the stolen tobacco.
- This story was first published on the Otago Daily Times website.