Born in Bootle, Merseyside, and started playing football at the age of 3. By the time Jamie was 7, his parents had to tell a ‘ white lie’ and say he was 8 so he could start playing for Sunday league team Merton Villa in Bootle and Litherlands District League where he played for 7 years, before being selected to play for Sefton Borough. Jamie’s talent was spotted and he attended the FA’s school of excellence in Lilleshall at the age of 14.
Although a childhood Everton supporter, he joined Liverpool’s School Of Excellence in 1988. Jamie spent a year at the Everton School of Excellence at the age of 11, but returned to Liverpool due to the club’s superior coaching set-up under Steve Heighway.
At the age of 16 he signed a YTS contract at Liverpool FC. He failed to impress in his first appearances to the Liverpool A and B teams due to his then-small stature, but after being moved from up front to a midfield role he was able to establish himself in the reserve team.
He played his first game for the reserves in the 1994–95 season, and was named man of the match against Blackburn Rovers at Haig Avenue.
He helped Liverpool to win the 1996 FA Youth Cup with a 4–1 aggregate victory over a West Ham United side that included Rio Ferdinand and Frank Lampard.
Jamie was tried out in defence for the first time during the tournament, and later admitted that Liverpool were not the most technically gifted side in the competition, but instead relied on team spirit and the outstanding talents of Michael Owen.