Montgomery started his career at the Western Bulldogs, moving to Port Adelaide in 1999 where he was part of the convoluted trade that also saw former Melbourne defender Matthew Bishop join the club, while Nathan Eagleton headed to the Dogs. He debuted for Port Adelaide was in Round 1, 2000, playing with the side until the end of 2005, when he was redrafted by the Bulldogs. During his time at Port he took out the John Cahill Medal in 2000, made the All Australian side in 2002 and represented Australia in the International Series against the Irish in the same year, and was a member of Port’s 2004 Premiership.

2000-2005 Statistics:
Games: 126
Goals: 51
Average kicks: 9.41
Average handballs: 7.13
Average disposals: 16.54
Average marks: 6.29
Average tackles: 1.45
Total Brownlow votes: 17

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