As part of the trade, it was believed that Melbourne would pay approximately $320,000 of Woewodin's salary in his first year at Collingwood and Collingwood would pay the balance of $180,000. In the second year, Melbourne and Collingwood were to pay his salary in equal shares and in his third year, Collingwood would shoulder most of his salary, thereby creating room in Melbourne's salary cap. Woewodin was informed of his trade to Collingwood while holidaying in Mauritius. Woewodin was understandably shattered to have been moved on without any significant warning. A verbal war of words between Woewodin and Melbourne coach Neale Daniher, in particular, continued until the Melbourne–Collingwood Queen's Birthday match of 2003. After publicly stating he hoped the Magpies would "smash" his old side, Woewodin got his "revenge", picking up 22 touches in the Pies' 52-point victory. It was the only time Collingwood defeated Melbourne during his three-year stint at the club. Woewodin's finest hour for Collingwood came in the round seven victory over Adelaide at AAMI Stadium, a night best remembered for Chris Tarrant's goal after the siren to clinch victory. Woewodin's hard running across the ground ensured that his 25 possessions and two goals earned him three of his 12 Brownlow votes for the season. 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. As Collingwood slid from contention in 2004 Woewodin enjoyed his best season in black and white, finishing second in the Copeland Trophy; however, the following season saw Woewodin fall out of favour. 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.