He made his debut mid-way through 1998 as a small-forward and played
most games since making his first appearance. He spent a further 2
seasons at the Dockers before being traded to Collingwood
in 2000. Holland quickly adapted as a good player with the Magpies and
became a fan favourite in his first season, kicking 28 goals in 21
matches.
In 2002 he started off with a 3-goal haul against Richmond and then produced an 8-goal haul a week later against the West Coast Eagles,
to be the leading goalkicker for the season after round 2. He then was
quiet for the rest of the season. He injured his back, causing a month
out of the game, but could not get back in the side until late season.
He was dropped after round 22 and missed the Magpies first finals
campaign since 1994, which included playing in the 2002 AFL Grand Final.
2003 saw him change to a tagging role in the midfield rather than the
inconsistent goal-kicking small forward. He had a clash with Scott Camporeale of Carlton leaving him with a bloodied nose, while late in the year, he was suspended for punching Paul Williams of Sydney in the stomach. He missed the first final but managed to get back in for the Preliminary and Grand Final sides.
He continued as a tagging midfielder, despite some problems at the
tribunal during years 2004 and 2005, and his good form bought him very
close to winning the Copeland Trophy, coming second to James Clement in 2005.
While he could not retain his 2005 form, he continued to be a fan
favourite in 2006, showing grit and determination to win the ball,
highlighted in a match against the Geelong Football Club, in which he bravely laid a huge tackle on Geelong big man Cameron Mooney.
In the Elimination Final against the Western Bulldogs, Holland was suspended for 6 weeks for rough conduct against Brett Montgomery.
Montgomery who was injured in the clash returned to the field and went
on to kick 6 goals to lead the Bulldogs to an inspiring victory.
After playing just 1 game in 2008 due to injury, Holland was delisted
by Collingwood. He was hopeful of continuing his career at another AFL
club but was not picked up, he then retired.
