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.

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 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.

In the Elimination Final against the Western Bulldogs, Holland was suspended for 6 weeks for rough conduct against Brett Montgomery.

The regulations of AFL Victoria, the sport's governing body, say that a player who has served more than 16 weeks' suspension in one competition cannot transfer to another.

In November 2022, the Northern Bullants club appointed Holland as their coach for the 2023 Victorian Football League (VFL) season.

Holland resigned as coach effective immediately shortly after the club's final game of the season.