He began his career with Premier League side Manchester United in 1995 but was released two years later after failing to make a first-team appearance. He joined Preston North End for £250,000 and managed to notch up 63 goals in 189 league matches until his departure to Manchester City in 2002. Macken eventually made his first Premier League appearance for City. He only managed to score seven goals in 51 appearances during his three years with City but notably scored against United in the Manchester derby in 2004. He signed for Crystal Palace in 2005 and while there, moved to Ipswich Town on loan. In 2007, he moved again to Derby County but was loaned out to Barnsley after failing to make an impact at Pride Park where he failed to score in 11 league appearances. He joined Barnsley permanently in 2008 and moved again to Walsall two years later. He was released by the Saddlers at the end of the 2011–12 season and joined Northern Premier League side Northwich Victoria, before joining Stockport County briefly in 2013.