Jim Brennan left Newmarket, Toronto for Britain in 1994 at the age of 17, hoping to establish himself and start a career in soccer. He signed with the youth team of Bristol City in the Second Division, and made his debut in the October of 1996, against Bournemouth. Jim signed for Nottingham Forest in 1999 for 1 and half million pounds, setting a transfer-fee record for a Canadian-born player. He made over a hundred appearances for Forest before joining Norwich City. Whilst with Norwich, Jim was part of the squad the won the Championship title, winning promotion back to the top flight. The following season, Jim became the first Canadian outfield player to play in the Premier League. In 2007 he was Toronto FC's first ever player, as the first captain. He stayed with his hometown club, earning a 2008 All-Star nomination, before retiring in 2010 to take up various administrative and coaching roles within the Toronto organization. He would leave the club in 2014, taking up the Executive Director position at Aurora Youth Soccer Club. Brennan would make 49 appearances for Canada over the course of his career, scoring 7 times. He was part of the team that won the 2000 CONCACAF Gold Cup, competed in the 2001 Confederations Cup, and earned a bronze in the 2002 CONCACAF Gold Cup.