Following this success, Macken moved into the Premier League with a transfer to Manchester City in February 2002, for a fee of £5,000,000. He is most remembered at City for scoring the winner in the 4-3 comeback win against Tottenham in the 2003–04 FA Cup on 4 February. However, he was severely hampered by a succession of injuries, and only made 27 league starts in over three years. This downturn in his career brought about a move away from Manchester and Macken joined Crystal Palace in the summer of 2005 for £1,100,000.