McFadden started his playing career with Motherwell, where he came to prominence in the 2002–03 season by scoring 19 goals and winning the Scottish PFA Young Player of the Year award. Everton signed McFadden for £1.25 million in 2003. McFadden struggled to hold down a regular place in the Everton first-team and moved to Birmingham City for £5 million in January 2008. A serious injury meant that McFadden missed most of the 2010–11 season and the "Blues", who were relegated in his absence, decided not to renew his contract. McFadden signed again for the "Toffees" on a free transfer in October 2011, after regaining his fitness, and spent three months with Sunderland in 2012.