The Sydney-based Bulldogs liked what they saw in him following a trial and he played for their Under-20s team in 2009 and 2010.
But despite an enjoyable experience across the Tasman, the lines weren't biting on a professional deal so he returned to Palmerston North and linked with the Old Boys-Marist club as he switched his focus back to rugby.
He began a bachelor of business studies with Massey University - he still hasn't got past the first year papers - as the lure of a Manawatu contract spurred him along.
Then-coach Dave Rennie liked what he saw and Milner-Skudder made his debut for the Turbos in 2011, a season where they charged to the Championship final in the ITM Cup on the back of a stellar campaign from first-five Aaron Cruden.
"I didn't think I'd be making the All Blacks and things like that," Milner-Skudder said of his decision to return to New Zealand. "I was just taking it one step at a time. There were a few awesome players going around in Manawatu back then so it was awesome just to be in that set-up and learning off those guys and getting a crack for Manawatu."
Injuries plagued Milner-Skudder for the next couple of years - he made only five appearances for Manawatu in the 2013 ITM Cup - but his talent was clear. He has since switched his allegiance to Varsity at club level and squeezed in a few games for them last year.
Milner-Skudder joined the Hurricanes as a wider training group member last season and skipper Conrad Smith said he caught the eye of the senior players on the training paddock.
"He's got a good head on him and he makes the right decisions and his skills are pretty apparent. They'll get him a long way," Smith said.
The 2014 provincial competition was where everything clicked for Milner-Skudder. Manawatu charged to the ITM Cup's Championship crown and the Palmerston North lad was a constant threat at fullback for the Turbos.
He was one of the big movers in pre-season at the Hurricanes, a franchise he arrived at on a full-time contract this year with no guarantee of a starting spot.
In a backline full of All Blacks, the No 15 jumper was available at the Hurricanes with Jason Woodward and James Marshall the other contenders.
By April, the competition was closed. Milner-Skudder made 13 appearances during the season and scored four tries along the way. He also made 21 clean breaks, beat 44 defenders and proved adept on the right wing.
His form proved irresistible for the All Blacks selectors and coach Steve Hansen has said that every player that was named in the 41-man squad last Sunday would get a chance to stake a claim for a World Cup spot in the coming months.
"It's nice to know you'll be in the mix somewhere and hopefully get a crack at some stage," Milner-Skudder said. "So, I'm looking forward to getting in that environment and learning a whole lot and helping my game go up another gear."
Before he links with the All Blacks he has some Super Rugby business to attend to as the Hurricanes host the Brumbies in their semifinal clash in Wellington tonight.
The prospect of a maiden home grand final looms next week.
