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 whilst 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.
Macken represented the England U-20 team at the 1997 FIFA World Youth Championship, earning one cap.
He scored over 70 goals at Preston, twice winning the Player of the Year award. In 1999-2000, under David Moyes, 25 goals from Macken saw Preston win the Second Division title.
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.
However, things turned upwards from there. Poor form by Morrison in the run-up to the Christmas period gave Macken his chance, and he scored his first competitive goal for Palace in the game at Coventry City, on 14 October 2005 (he had previously scored in a pre-season friendly), and scored again on 26 December, at Ipswich Town, although he was later sent off.
Torghelle left permanently for Greece, but again his playing opportunities were limited. On deadline-day of the Summer 2006 transfer window, he made a further move to Ipswich Town in The Championship, this time on loan, being handed the number 27 shirt. The loan was finally agreed when Ipswich agreed to pay an increased proportion of his wages. Macken scored three goals for the Tractor Boys before returning to Selhurst Park.
Macken initially joined Barnsley on 1 November 2007, on loan from Derby County. He made his debut against the club that made his name, Preston North End. He remained goalless for his first nine games, despite having produced a string of fine performances. On 22 December, he scored his first Barnsley goal against promotion chasing Bristol City after a fine run and shot.
He made a couple of substitute appearances for the Rams but his inevitable return to Barnsley was secured on 28 January 2008 for £200,000.
He was released by Barnsley after the 2009–10 season and left when his contract expired in June.
On 19 August 2010, League One club Walsall signed Macken on a one-year deal with the option of a further year. On 9 May 2012 it was announced that Macken had been released by Walsall.
On 9 October 2012 it was reported that Macken had signed for Northwich Victoria. He made his debut for the club in a 1–1 draw at Newcastle Town, as an 80th-minute substitute, that evening.
Macken made his Stockport debut as a second-half substitute in County's 3–2 home win over Nuneaton Town on 2 February. He scored his first goal for the club against rivals Macclesfield Town on 30 March. Following their relegation from the Conference National, he was released.
On 24 February 2015, Macken came out of retirement to sign for Bamber Bridge. He made his debut in a 2–1 defeat to Darlington 1883 on 28 February.
In September 2017 he was appointed as manager of non-league club Radcliffe Borough.
