Hall kicked his 600th career goal against the Western Bulldogs in Round 10, 2009, when he kicked six in that game. After a striking incident involving Adelaide's Ben Rutten in his 250th game, Hall was put under an immense amount of pressure from coach Paul Roos to leave the club. Hall called a press conference on 7 July 2009 to announce that he was no longer going to play for the Swans. He kicked four goals in his last game for the club.
It was announced on 6 October 2009 that the Western Bulldogs had agreed to trade draft pick 47 for Hall with Sydney. On his Bulldogs' debut, in the second round of the 2010 NAB Cup, he kicked six goals against Hawthorn. He then kicked four goals against Port Adelaide and had a part in the final and winning goal which gave the Bulldogs a place in the NAB Cup grand final against his first club, St Kilda. In the final he kicked seven goals, including five in the last quarter, to lead the Bulldogs to their first grand final success of any kind since 1970. He was awarded the Michael Tuck Medal for best on ground. He made his home-and-away debut for the Bulldogs in Round 1 against Collingwood at Docklands Stadium, but his side were defeated by 36 points. Hall kicked three goals.