Scotland was initially given guernsey No. 44, and he switched to No. 29 in 2001. He made his debut in Round 3 of 1999 and played twelve senior matches in his debut season, including Collingwood's Round 22 match, which was the last game it ever played at its traditional home ground, Victoria Park. He played another ten in 2000, but managed only two senior games in 2001 – in the first and last rounds of the season. His performance in that final round match, to that stage a career-best with twenty-eight disposals, arguably saved his Collingwood career, with coach Mick Malthouse stating that he had matured considerably as a footballer over that season.