Jermaine Pennant played his youth football for his local team Notts County. Arsenal paid £2 million for Pennant, who was 15-years-old, in 1999, a record fee for a trainee at the time. Pennant made his debut for the Arsenal first team in the League Cup against Middlesbrough, at the age of 16 years and 319 days, which made him Arsenal’s youngest-ever first team player (Cesc Fabregas and Jack Wilshere have since surpassed this record). In his first Premier League start for Arsenal in May 2003, Pennant scored a hat-trick against Southampton. However, those three goals were also Pennant’s only ever League goals for Arsenal. Arsenal ended up winning the game 6-1. Also, despite 24 caps with the England under 21’s, Pennant was never capped for the senior team.

Arsenal manager Arsène Wenger became frustrated with Pennant’s attitude, as he would often turn up to training late and would moan about not playing. Bear in mind that the team he was part of consisted of most of the 2003/2004 league winners, the famous ‘Invincibles’. So, after loan spells at Watford, Leeds United and Birmingham City, Pennant left Arsenal for Birmingham permanently in 2006, for a fee of £3 million, and ultimately failed in fulfilling his potential at the Gunners.

While at Birmingham City permanently, Pennant made 38 appearances and scored two goals for the Blues, but could not prevent the team from being relegated. While there, Pennant played a game with an electric tag around his ankle, after he was convicted for drink-driving. However, due to his impressive performances throughout the season, he was rewarded with a £6.7 million move to Liverpool in 2007. Whilst at Liverpool, Pennant won the FA Community Shield and was part of the squad who took Liverpool to the 2007 Champions League Final, which resulted in a 2-1 loss to AC Milan. He then, however, fell out of favour, with his negative off-pitch exploits often being reported in the national newspapers. He left Liverpool as a costless agent and went to Spain, to play for Real Zaragoza in 2009. His time at Zaragoza was turbulent, to say the least. He was reprimanded for his lateness to training by then-coach Jose Aurelio Gay in February 2010. He never played for the team again. He was then loaned to Stoke City the subsequent summer. 

His time at Stoke, from 2010 to 2014, was one of both successes and failures. It started well, with Pennant becoming popular figure with the fans and boss Tony Pulis, due to his high-level of performance, as well as helping Stoke reach the 2011 FA Cup Final, which they lost 1-0 against Manchester City. However, like what had happened time and time again, his attitude let him down. He broke strict curfew twice for the club, and was subsequently loaned to Wolverhampton Wanderers in 2012 on a four-month loan, where he was even jeered by some fans for his poor performances. He returned to Stoke in January 2013 and continued to struggle. He was then released by Stoke at the end of the 2012-2013 season. However, after Pulis parted ways with Stoke, new manager Mark Hughes offered Pennant another chance at the club. Although he did score a great costless-kick against West Ham United in August, he made little impact during the 2013-2014 season and his contract was terminated on 24th January 2014.

Over nine months elapsed before the 31-year-old returned to football this month, with a move to Indian Super League outfit FC Pune City, a team created only this year. They are owned by Bollywood actor Hrithik Roshan and Italian football club AFC Fiorentina, and their captain is former French international and Juventus striker David Trezeguet. Pennant made his debut for Pune City on 15th November, in a 0-0 draw against North East United. When asked in a recent interview about his career, Pennant stated: “It's been a good journey. There have been a lot of ups and downs. But the most important thing is that I have enjoyed the football I have played. Now playing in India is a good challenge for me. It's a fresh world and offers a great amount of talent.”