Born in Nottingham, Pennant played for his local side Notts County as a teenager. He earned promising reviews in the youth team at County and Arsenal signed him in 1999. He struggled to make much of an impact at the North London club and spent time on loan at Watford, Leeds United and Birmingham City before joining the latter permanently. While an Arsenal player, he won 24 caps for the England under-21 team. He gained notoriety in 2005, when he had to play a match while on probation – he played while wearing an electronic tag following a drink-driving conviction. Following Birmingham's relegation in 2006, Pennant signed for Liverpool for a fee of £6.7 million. He won the 2006 FA Community Shield and also played a vital role in the club's run to the 2007 UEFA Champions League Final, where Liverpool lost 2–1 to Milan.