A Woodville-West Torrens 'best and fairest' winner in 1992, Pyman was secured by North Melbourne with the sixth pick of that year's draft, which they received after trading Paul Spargo to Brisbane – although Pyman was later personally fined $10,000 when it emerged that he had contacted some of the league's struggling clubs and warned them that he would stay in South Australia if one of those clubs drafted him, which contravened the AFL's draft tampering rules.
In 1996 he crossed to Collingwood but again struggled to play senior football, despite winning the Joseph Wren Memorial Trophy as the best and fairest of the reserves.
Pyman's final port of call was Melbourne and for the first time in his career he was a regular in the AFL, playing 19 of a possible 22 games.
He received the only Brownlow votes of his career in the same season when he was adjudged 'best on ground' in a loss to Sydney at the SCG, for getting 18 kicks and eight handballs.
Pyman steered the SANFL club to fourth position in his third year but after a string of poor performances was sacked and replaced by former Geelong player Gary Cameron late in the 2007 season.