Jonathan Macken was born September 7th 1976 in Manchester. He was signed on as an apprentice with Manchester United in 1996, but joined Preston North End the following year along with Mike Appleton and Colin Murdock in a deal worth £1 million. He scored 25 goals in Preston's Second Division Championship-winning season in 2000, including a famous chip over David Seaman in a 3rd-round Worthington Cup game against Arsenal, and in 2001 he scored 22 goals and was named in PFA Divisional team by his fellow professionals.
In 2002 he had another good season with Preston, where he scored a memorable long-range effort in the 2-1 home success over Manchester City on October 21. By then he was beginning to set his sights on higher grounds and put in a transfer request at Deepdale. After scoring another 11 goals Manchester City and Preston agreed a £4 million fee with the prospect of rising to £5 million depending on appearances.