15th Jan 1983
After leaving All Whites Pennant played for his local side Notts County as a youngster. He earned promising reviews in the youth team at County and Arsenal signed him in 1999. While an Arsenal player, he won 24 caps for the England under-21 team. . 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.
However, off-field problems continued to affect Pennant and consequently led to him being left out of the side. He joined Portsmouth on loan before leaving to join Spanish side Real Zaragoza in 2009.
His time in Spain was overshadowed by disciplinary problems. He returned to the Premier League for the 2010–11 season signing on loan at Midlands club Stoke City. Following a successful loan spell, he signed a permanent contract at Stoke in December 2010.
He played in the 2010 FA Cup final, Stoke losing 1–0 to Manchester City, and also played in the UEFA Europa League the following season.
He then spent time playing in India with Pune City before returning to England to sign a short-term contract with Wigan Athletic. In January 2016, he signed a one-year deal with Singapore S.League club Tampines Rovers.