Round, the son of former Brownlow Medal winner Barry, was drafted by the Western Bulldogs under the father–son rule.
[2] Having been delisted at the end of the season, Round was rookie listed by North Melbourne.
In 1999 he won Williamstown's "best and fairest" award but by 2001 was spending a lot of time in the reserves.
He performed so well in the 2001 VFL reserves competition that he took home the Todd Medal, as the league's best player.
[4] In 2002 he moved to Queensland to join Southport and was a Grogan Medal winner in his first season.