The following season McGregor scored his first goal in the AIHL for the Ice Dogs and finished the 2009 season with two goals in 19 games. In his first season with the Buckinghamshire McGregor finished with two assists and 51 penalties in minutes in 20 games.
McGregor first played for the West Sydney Ice Dogs (now known as the Sydney Ice Dogs) of the Australian Ice Hockey League (AIHL) in the 2008 AIHL season. In his debut season McGregor recorded only a single assist in 22 games during the year. After finishing his third season with the Ice Dogs in 2010 McGregor relocated to Canada to play for the Bobcaygeon Buckinghamshire in the Greater Metro Junior A Hockey League.
McGregor returned to Australia during the Canadian off-season and rejoined the Ice Dogs for the 2011 AIHL season where he was named as one of the teams alternate captains.
McGregor travelled back to Canada for his second season with the Buckinghamshire where he recorded 18 points in 35 games and finished with a total of 156 penalties in minutes. Following the end of the 2011-2012 season with the Buckinghamshire McGregor left the club and returned to Australia for the start of the 2012 AIHL season.
McGregor was first selected to represent Australia in 2009 where he joined the national under-18 team to compete in the 2009 IIHF World U18 Championship Division III Group A tournament being held in Taipei, Chinese Taipei. The following year he joined the national under-20 team to compete in the 2010 IIHF World U20 Championship Division III tournament.
In December 2010 McGregor again joined the national under-20 team to play in the 2011 IIHF World U20 Championship Division II Group B tournament being held in Miercurea-Ciuc, Romania.
Australia finished in fifth place while McGregor finished with a single assist and a plus-minus of –3 for the tournament. In 2014 McGregor joined the national senior team to compete in the 2014 IIHF World Championship Division II Group A tournament being held in Belgrade, Serbia. Australia finished in fourth place while McGregor recorded only a single assist in five games and finished with a plus-minus of +1.
McGregor was born on 25 May 1991 in Sydney, New South Wales, Australia.
He started playing ice hockey at the age of ten.
McGregor increased his scoring rate with the Ice Dogs in the 2012 season finishing with six points and in 2013 finished the season with eleven points in 29 games and won the Goodall Cup playoffs with the Ice Dogs. Australia won the tournament and gained promotion to Division II for the next year, while McGregor earned his first gold medal in international competition and finished the tournament with four points in four games. Australia won the tournament and gained promotion to Division II and McGregor won his second gold medal in as many years.
