Birthdate: 15 January 1983
Birthplace: Nottingham, England
Other clubs: Arsenal (1999-2005), Watford (loan 2002 + 2002-03), Leeds United (loan 2003-04), Birmingham City (2005-06), Portsmouth (loan 2009), Real Zaragoza (2009-10), Stoke City (2010-14), Wolverhampton Wanderers (loan 2012-13), Pune City (2014), Wigan Athletic (2015), Tampines Rovers (2016-)
Bought from: Birmingham City
Signed for LFC: £6.7m, 26.07.2006
International caps: u-21 24/0 caps/goals
Liverpool debut: 09.08.2006
Last appearance: 29.10.2008
Debut goal: 20.01.2007
Last goal: 19.04.2008
Contract expiry: 01.07.2009
Win ratio: 58.02% W: 47 D: 18 L: 16
Total games/goals opposite LFC: 12 / 0
LFC league games/goals: 55 / 3
Total LFC games/goals: 81 / 3
Pennant became the most expensive teenager in history when he signed for Arsenal for £2million from Notts County in January 1999. Arséne Wenger is a master at turning youngsters into full-fledged professional footballers, but couldn't handle the rebellious Pennant who was discovering the bright lights of London. He only played 26 games for Arsenal in six and a half years, his highlight a hat-trick in a 6-1 win over Southampton in the Premier League in May 2003. Those three goals turned out to be his only ones for the club. Pennant was shipped out to other clubs and finally Birmingham was impressed enough to pay £3 million for him on 1 July 2005. He had been on loan at Birmingham since January and during this time he turned in some impressive performances, but also served 30 days in jail for driving under the influence with a suspended license! Rafa decided to gamble on the right-winger after an impressive 2005/06 season as he thought he was mature enough to star for his boyhood favourites. Pennant made the highest number of appearances by any Liverpool player, 52 in total, in his debut season but there was still room for improvement in terms of number of assists and goalscoring. His only goal up to that point was though a tremendous one against Chelsea at Anfield. Pennant started the next season in similar vein, the only blot on his copybook a silly red card against Porto in the Champions League in September. He received an injury in his next group stage game, at Besiktas, and was sidelined for a couple of months. On his return he didn't start as many games as he was used to. Once the 2008/09 season got under way, it became clear that Pennant was not likely to figure much in the manager's plans. He started only three matches in the first half of the season, with one more brief appearance coming as a substitute at Everton at the end of September. On 20 January 2009 he was loaned to Portsmouth for the remainder of the season. Pennant became a free agent on the opening day of July 2009 and a week later he joined Real Zaragoza, who had just been promoted back to Spain's top division.
Pennant appeared in 25 La Liga matches in a struggling team. He was also disciplined by Zaragoza for turning up late for training three times over a two-week period. After a single season in Spain Pennant returned to English football when he agreed to a four-month loan deal with Premier League club Stoke City which led to a permanent contract. Pennant's career was revived after joining Stoke and the Potteries reached the final of FA Cup for the very first time in 2011, but were left disappointed at Wembley as Manchester City won the cup. Pennant had a decent second season, but he still seemed plagued by personal problems that have curtailed his great natural ability. As Tony Pulis had no longer use for him at Stoke he was loaned to Wolves in the Championship for the 2012/13 season. Jermaine seems to revel in the lifestyle modern footballers enjoy. In fact, Real Zaragoza contacted their former player after city authorities called them about an abandoned Porsche 911 Turbo, with a P33NNT vanity number plate, which had been parked at a local rail station for five months. Pennant, who owns a number of sport cars, had apparently forgotten all about the Porsche! Maybe his penchant for luxury is understandable if you consider he grew up in one of the worst neighbourhoods in Nottingham. The eldest of four children he brought up his siblings, after his mother left, until he was 15 and had little schooling, lacking basic skills in reading and writing. His father was sentenced to five years in prison in 2008 for selling crack cocaine and heroin.
After playing in only one early-season match for Stoke in 2012/13, Pennant went on loan to Wolverhampton Wanderers. Unfortunately, he joined a struggling team and although he played in fifteen matches in The Championship, Wolves were heading for a second successive relegation. Shortly after the end of the season incoming manager Mark Hughes, who had replaced Tony Pulis, announced that Pennant was one of seven players who were being released by the club. But less than two weeks later the club changed its mind and offered the thirty-year-old a new one-year deal. Pennant played in only eight Premier League matches for Stoke in 2013/14, all as a substitute, before his contract was terminated by the club on 24 January 2014. Pennant got back into football in November when he joined Pune City in the Indian Super League.
Following his brief flirtation with the Indian Premier League towards the end of 2014 the 32-year-old joined Championship club Wigan Athletic at the end of the third week in February 2015. He scored three goals in thirteen appearances but couldn't save them from relegation and although he was offered a contract he chose not to accept it but was unable to find a new club in time for the new season, a trial with Charlton coming to nothing. In January 2016 Pennant moved to Tampines Rovers in Singapore, with reports suggesting he was being paid triple the age of his teammates and provided with an apartment. After scoring one and providing four assists in eight games, he picked up an achilles injury in April but was hoping to be fit again for the resumption of the Asian Champions League in September.