Born in Nottingham, 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. 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.
However off the field problems continued to affect him 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 2011 FA Cup Final, Stoke losing 1–0 to Manchester City and also played in the UEFA Europa League the following season. Pennant fell out of favour with Tony Pulis in 2012–13 and spent time out on loan at Wolverhampton Wanderers. With his Stoke career looking to be coming to an end new manager Mark Hughes gave Pennant a new contract. However, after failing to make an impact he left Stoke in January 2014. He then spent time playing in India with FC Pune City before returning to England where he signed a short-term contract with Wigan Athletic. In January 2016, he signed a one-year deal with Singapore S.League club Tampines Rovers.
Pennant was born in The Meadows area of Nottingham, Nottinghamshire. His father was of Jamaican descent, his mother is British. His father Gary was a semi-professional footballer who inspired Pennant to play. His mother died from cancer when he reached three years of age. As a result, he helped raise his younger siblings, two sisters and one brother. Pennant recalls how as a child his favourite toy was a football, and how it rarely left his side.
Pennant, who grew up in a crime- and drug-infested neighbourhood, 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 a 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 second half of the 2004–05 season. He made a good start at St Andrew's providing Walter Pandiani with the winning goal against Southampton on his debut. Pennant then stated that he wanted to make turn his loan move into a permanent transfer. On 1 March 2005 Pennant was arrested and convicted for drink-driving, driving while disqualified and driving without insurance. He was handed a three-month prison sentence by the courts. Despite this Birmingham manager Steve Bruce and chairman David Gold vowed to stand by Pennant once his sentence was over. He was released from prison after serving 30 days and wore an electronic tag in a match against Tottenham Hotspur.
Pennant signed a permanent contract with Birmingham on 25 April 2005 for a fee of £3 million. Pennant again struggled with discipline problems in 2005–06 as the team battled against relegation. Birmingham were relegated to the Championship after they drew 0–0 with Newcastle United. Following Birmingham's relegation, Liverpool made a bid for Pennant.
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 Championship qualifying matches against Israel and Russia, despite the backing of Liverpool manager Rafael Benítez. 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.
On 9 July 2009, Pennant passed a medical and signed a three-year deal at Real Zaragoza. He made his La Liga debut first round of the season, and played for 71 minutes in Zaragoza's 1–0 win over CD Tenerife. The team had languished near the bottom of the table all season and his performances had also come into question, as he looked uncomfortable and still seemed unfamiliar with his surroundings. On 24 February 2010, he was reprimanded by coach José Aurelio Gay after turning up late for training three times in the space of two weeks; he was sent home on the third occasion and disciplined. He never played for "Los Blanquillos" again.
On 31 August 2010, the final day of the summer transfer window, Pennant agreed a 4-month loan deal with Premier League side Stoke City. Pennant made his debut for Stoke as a substitute in Stoke's home game against Aston Villa on 13 September 2010. Manager Tony Pulis indicated that he would look to make Pennant's loan switch permanent in the January transfer window. Pennant also expressed his desire to stay at Stoke after his loan spell.
Pennant joined Stoke on a permanent transfer on 29 December 2010 signing a two and a half-year contract for an initial fee of £1.725 million which could eventually rise to £2.8 million in the future.
"I think everyone knows how I feel about being at this football club. The supporters, players and management have been absolutely fantastic to me over these past four months and I desperately wanted to stay here because I love it so much. I know I have only been here a few months, but it really does feel like I have been here for years. The atmosphere around the place is brilliant, so I am looking forward to the fact that I am here at Stoke now for the long term and back in the best league in the world."
Following his transfer manager Tony Pulis stated that Pennant must not become complacent. He scored his first goal for Stoke in a 4–0 win over Newcastle United in March 2011, contributed an assist in their 5–0 defeat of Bolton Wanderers in the FA Cup Semi-final, and scored his second goal of the season as they beat Wolves 3–0 a week later. He also scored against his former club Arsenal. Pennant played in the 2011 FA Cup Final as Stoke lost 1–0 to Manchester City.
Pennant was handed the number 7 shirt prior to the start of the 2011–12 season. However, he reverted to number 16 as a large number of fans had already purchased a replica shirt with his name and old number on the back. Pennant went on to have an up and down season as he played in 40 of the clubs 59 fixtures (starting in 23) helping the side reach the last 32 of the UEFA Europa League and the quarter final of the FA Cup. But off the pitch problems dominated Pennant's season as he broke a club curfew twice, before matches against Everton and Crawley Town. This led to speculation over his future at the club but Pennant insisted he was not looking to leave the Britannia Stadium.
However, with the arrival of Wolverhampton Wanderers winger Michael Kightly, Pennant was unable to force his way back into Tony Pulis's plans and on 12 October 2012, he moved to Wolves on an emergency three-month loan deal. He did not have the best of spells at Molineux making just ten starts and was jeered by some of the Wolves support for some poor performances and returned to Stoke in January 2013. After returning to Stoke Pennant had found himself out of the first team and looked to be leaving Stoke at the end of the 2012–13 season after the deadline for a new contract expired. He was released by Stoke at the end of the 2012–13 season. However it was revealed that new Stoke manager Mark Hughes had offered Pennant a new contract. Pennant accepted the offer signing a new one-year contract on 18 June 2013.
Pennant returned to the side for the 2013–14 season and on 31 August 2013 he scored a free-kick against West Ham United in a 1–0 victory. However, after making little impact under Hughes his contract was terminated on 24 January 2014.
On 6 November 2014 Pennant joined Indian Super League side FC Pune City. He played seven times for Pune as they finished in sixth position.
On 21 February 2015, Pennant joined Championship side Wigan Athletic until the end of the season on a free transfer. Pennant played 13 times for the Latics and scored three goals, all of which were free-kicks, but was unable to help prevent Wigan suffering relegation to the third tier. He was offered a new contract with the club, but chose not to accept.
On 6 January 2016, Pennant went on trial at Singapore's Tampines Rovers FC. Ten days later, the club announced that Pennant would sign a 12 months contract with the club. As reported by the local media, he would earn SGD$10,000 a week, a 70 percent pay cut from his last drawn salary at Wigan. On 26 February 2016, Pennant scored his first goal in a friendly match against Hougang United FC from a free kick. Pennant would go on to score against Home United FC and against Warriors FC.
Pennant signed a short-term contract with League One side Bury on 19 January 2017.
Pennant had a trial spell with Scottish Premiership club Hibernian during July 2017, but the club decided against offering him a contract. He then signed a two-year deal with Isthmian League Premier Division side Billericay Town.
Whilst on the England under-21 team, he was sent home by coach David Platt for breaking a curfew before an important game against Turkey. He later apologised for his actions. He also was sent off for punching Niko Kranjčar in a game against Croatia under-21s. However, he did manage to make 24 appearances for the U21s in total, making him one of the ten most-capped Englishmen at this level.
Despite being of Jamaican and Irish descent, he has so far opted to represent England internationally; although he has played at under-21 level, he has not played for the senior team. In March 2011 Pennant revealed that though he would still "love to play for England", he had made the Football Association of Ireland aware that he was interested in representing the Republic of Ireland, saying "if I've got a chance to play international football with Ireland, I'm going to take it with both hands".
Pennant plays as a right winger who has been described by former Newcastle United left-back José Enrique as a player with similar style to that of Aaron Lennon and Theo Walcott. Pennant is also able to use skill to beat opponents' full backs.
In February 2004, Pennant was given a sixteen-month ban from driving after being seen driving in the wrong lane in Paddington, West London. On 23 January 2005, Pennant was arrested and charged with drink-driving after crashing his Mercedes into a lamp-post in Aylesbury, while serving a sixteen-month driving ban and uninsured. During questioning, Pennant initially identified himself as his friend Ashley Cole. Pennant pleaded guilty to drink-driving and driving while disqualified, and he was sentenced to ninety days in prison on 1 March. He was released on parole after 30 days and immediately returned to playing for Birmingham, although he had to wear an electronic tag at all times, including while on the pitch. It emerged during the trial that he was illiterate.
In January 2011 Pennant's Porsche Turbo with his personal number plate was found abandoned at a railway station in Zaragoza with five months' worth of parking tickets. He was reported to have forgotten he owned the car. In April 2012 Pennant was arrested for drink driving, driving while disqualified and without insurance after being involved in a traffic collision. The following month he was banned from driving for three years and given an eight-week jail sentence, suspended for a year.
In 2007, Pennant began dating glamour model Amii Grove. Following a domestic disturbance in July 2007, Pennant was arrested for a Section 5 public order offence – using words or behaviour likely to cause distress – for which he had to pay a fixed penalty fine. According to Grove, she ended the relationship upon finding CCTV footage of Pennant cheating, and "took revenge by destroying £200,000 of his designer gear". In December 2008 Pennant's front gates at his home in Cheshire was ram-raided by burglars in an attempted robbery.
Until January 2008, Pennant was dating Hollyoaks actress Jennifer Metcalfe. In October 2008, he reunited with former girlfriend Amii Grove following the death of her brother and became engaged. Soon afterwards, Pennant's father Gary was convicted on drug dealing charges and sentenced to four years imprisonment. In early 2009, Pennant and Grove broke up and Pennant began dating Metcalfe again. Following his move to Spain, Pennant broke up with Metcalfe but the pair remain friends.
In May 2010 Pennant became engaged to Lara Murphy. and they have a son named Trey who was born in August 2010. The relationship with Murphy ended when his son was a year old, when Pennant left her for glamour model Alice Goodwin. He married Goodwin in May 2014.As of match played 5 April 2017
FA Community Shield: 2004
FA Community Shield: 2006
UEFA Champions League: Runner-up 2006–07
FA Cup: Runner-up 2010–11