The highlight of Woewodin's career is his 2000 Brownlow Medal victory, in which he finished ahead of favourite Scott West of the Western Bulldogs.
Woewodin held general discussions with Collingwood initially, but the media speculated that he was keen to remain in Melbourne and ultimately would accept a reduced salary.
In the days and weeks following his trade, it was revealed that Melbourne approached Woewodin at the end of the season with the view of negotiating a salary reduction.
From there, Woewodin enjoyed a steady first season at Collingwood as the Pies continued on from their stellar 2002 form to once again meet the Brisbane Lions in the Grand Final.
Despite kicking Collingwood's first goal of the match, Woewodin was quiet on the day – as were a number of his teammates – and the Lions ran out convincing 50-point winners.
Prior to this game, he had stated to the press that he thought Neale Daniher getting rid of him was a blessing in disguise and that he was happy that he was going to play in a premiership this time (rather than a grand final).
With Collingwood winning a mere five games, the club's selection committee opted to pursue a youth policy, which saw the likes of Woewodin, whose lack of leg speed saw him unable to dominate the midfield as he once had, Andrew Williams and, to a lesser extent, Matthew Lokan, ushered out of the side.
On the Queen's Birthday match between Melbourne and Collingwood on 12 June 2006, Shane Woewodin did a pre-match lap of honour in an open-top car with his children to celebrate his distinguished career with both sides.
In an interview he gave prior to the game, he continued to signal his intent to return to the AFL in 2007 and was doing "all the right things" with East Fremantle in an attempt to catch the eye of recruiting staff.
It was rumoured that Woewodin was asked to play in the annual E. J. Whitten Legends Game with all the other past players, but refused – apparently because he felt that it would completely ruin his chances of being drafted in 2007.