Jackson is also a former New Zealand rugby union player. During his playing career, he was a first five-eighth. Domestically, he represented Bay of Plenty and Waikato in the Non-Player Character and the Saracens in the United Kingdom"s Guinness Premiership.
His strong performances saw him named in the Chiefs squad for the 1999 Super Rugby season and had international experience as well with the Māori All Blacks and the Barbarians.
He made his debut for the Chiefs in the opening round of the 1999 Super 12 season. Jackson made his final appearance for the Chiefs in a 2004 Super 12 semi-final defeat to the Brumbies.
He signed for Saracens in 2004. In 2007 he was voted The Professional Rugby Players" Association player of the year after being leading points scorer in the 2006-2007 Guinness Premiership.
In 2009 he played for the Barbarians.
Jackson played his final game for Saracens against Leicester Tigers in the final of the 2009-2010 Guinness Premiership. In 2010 Jackson retired to become a professional referee in his native New Zealand. He was fast-tracked into the professional rugby ranks by Lyndon Bray, then the head of referees for the New Zealand Rugby Union and now in the same role with SANZAAR, organiser of Super Rugby and The Rugby Championship (formerly the Tri Nations).
On the 15th February 2015 he made his Six Nations refereeing debut when he took charge of the Scotland-Wales match at Murrayfield.
Jackson was the first New Zealander to play and referee 100 first class fixtures when he took charge of the Argentina v South Africa match on 15 August 2015.