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He would not play for any other region now but the route south took some fairly significant detours.
The 24-year-old lives in Auckland and makes a living taking people out on chartered fishing trips. He was born in Christchurch but moved to Australia with his family when he was very young. He returned to New Zealand and moved to Tauranga to study and has a diploma in marine studies.
He kept his hockey up and took an opportunity to play for the Southern Dogs in 2010 and earned selection for New Zealand that year.
"The first time I played in a New Zealand league it was for Southern so therefore that created me as a Southern Dog," he said.
While McGregor was not born or bred in the region he felt comfortable in the environment and says he is a "Southern Dog at heart" and "wouldn't play for anyone else".
McGregor has close friendships with Southern and Black Sticks team-mates Blair Tarrant and Hugo Inglis.
The trio flatted together in Auckland earlier this year and after the Olympics Games McGregor and Inglis took the opportunity to travel around Europe together.
While they were getting some overseas experience, Southern was surprising everyone with its run in the National Hockey League. The Dogs won their way through to the final before coming unstuck against Auckland.
It was a great campaign but while the wider hockey community was taken back by Southern's rapid rise, McGregor said he was not surprised the team had performed so well.
"They've got a fantastic group of young guys with Kane Russell, Nick Elder and Jeremy Morris. They are all in the under-21 [New Zealand squad]. So there is a good bunch of young guys and also you've got guys like Blair Tarrant and James Nation at the back, so the defensive structure is really good.
"I knew they'd be a strong team and it is just unlucky they didn't win the final but there is always next year."
McGregor made his only appearance for New Zealand against Japan in 2010 and has had to play second or even third fiddle behind regular keeper Kyle Pontifex.
But Pontifex has made himself unavailable and that has opened the door for McGregor to add to his one international cap.
He has been selected in the Black Sticks side which will contest the Champions Trophy in Melbourne next month.
"With a new coach [Colin Batch] there is always going to be new opportunities but then again there is a lot of young guys coming through.
"But there is an opportunity for me to lay my claim, so hopefully I make the most of it."