Jermaine Lloyd Pennant, born 15 January 1983, is an English footballer who plays for Stoke City in the Premier League, on loan from Spanish club Real Zaragoza. 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.

Jermaine Pennant was born in Nottingham, England to parents of Jamaican descent. His father Gary was a semi-professional footballer who inspired Pennant to play. At age three, Pennant's mother died of cancer. As a result, he helped raise his younger siblings, two sisters and one brother. Pennant recalls how as a child his favorite toy was a football, and how it rarely left his side.

Pennant, who grew up in a crime and drug infested neighborhood, credits football for saving him from a life of crime. When he was 14, he moved away from home and was living with YTS players who were 16,17, and 18. Notts County provided Pennant a safe haven.

Pennant was signed at the age of 15 by Arsenal from Notts County for £2 million, a record fee for a trainee at the time, but failed to fulfil his promise amidst a string of disciplinary problems.

Pennant's career seemed promising following his move to Arsenal. He made his debut aged 16 years and 319 days against Middlesbrough in the League Cup on 30 November 1999, making him Arsenal's youngest-ever first team player, beating Gerry Ward's long-standing record by two days. Pennant's record has since been surpassed by Cesc Fàbregas and Jack Wilshere. He continued to make League Cup appearances over the next few seasons, but had to wait two-and-a-half years for his league debut, as a substitute against West Ham United on 24 August 2002 in the Premier League.

At first, Pennant became homesick. After that subsided, he began to get sick from not playing. It affected him greatly. He played for Arsenal for seven years and only made five starts including the hat-trick on his full league debut, against Southampton in May 2003. However, these were also his only Arsenal league goals and he did not manage to secure a regular place in an Arsenal side that went on a run of 49 consecutive games without defeat. Arsenal manager Arsène Wenger appeared to have eventually lost patience with Pennant, who had a history of turning up late to training. Between 2002 and 2004, Pennant spent time on loan at Watford and Leeds United. Pennant received regular first-team action at Leeds, who were relegated at the conclusion of the 2003-04 season.

Pennant was loaned to Birmingham City for the 2004-05 season. During his spell at Birmingham, he was arrested and convicted for drink-driving, driving while disqualified and driving without insurance. Despite his conviction, Pennant signed a permanent contract with Birmingham in April 2005. Following the 2005-06 season, Birmingham were relegated to the Championship, and speculation grew that Pennant would leave the club.

Pennant signed for Liverpool on 26 July 2006, on a four year contract for a fee of £6.7 million, potentially rising to £8 million with add-ons. After impressing in pre-season, Pennant made his Liverpool debut against Maccabi Haifa in a Champions' League 3rd round qualifying match at Anfield where he went on to win the fans' Star Man award. On 20 January 2007, he scored his first goal for Liverpool in their 2–0 home victory over Chelsea in the Premier League. On 31 March, Pennant participated in a 4-1 win against his former club Arsenal. After not being chosen for the England squad to play Israel and Andorra in March 2007, Pennant expressed the lack of recognition from England manager, Steve McClaren, as 'frustrating'.

Pennant started the 2007-08 season in good form, putting in strong performances on either flank as Liverpool reached the top of the league table in the first month. He was however, again ignored by McClaren for the England team in their European qualifying matches against Israel and Russia, despite the backing of Liverpool manager Benitez. As Liverpool struggled to regain their good early season form following the international break, Pennant too could not maintain his form. On 18 September 2007, Pennant was sent off against FC Porto in Liverpool's opening Champions League match of the season.

In January 2009, Pennant was loaned out to Portsmouth, where he spent the second half of the 2008-09 season. He played 13 league games for Portsmouth without scoring a goal. Pennant was not offered a new contract by Liverpool following his return, and subsequently became a free agent when his contract expired on 1 July 2009.