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.

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 AC Milan.

He then spent time playing in India with Pune City before returning to England to sign a short-term contract with Wigan Athletic.

Pennant returned to England once more signing for EFL League Two side Bury, before retiring in non-league football with Billericay Town in 2017.

[5] Pennant was signed at age 15 by Arsenal from Notts County for £2 million,[6] a record transfer fee for a trainee at the time.

Arsenal manager Arsène Wenger appeared to have eventually lost patience with Pennant, who had a history of turning up late to training.

[25] After impressing in pre-season, Pennant made his Liverpool debut against Maccabi Haifa in a UEFA Champions League third round qualifying match at Anfield, where he went on to win the fans' Star Man award.

[28] Pennant started the 2007–08 season in good form, putting in strong performances on either flank as Liverpool reached the top of the Premier League table in the first month.

[29] However, he was 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.

[citation needed] On 18 September 2007, Pennant was sent off against Porto in Liverpool's opening UEFA Champions League match of the season.

[37] 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.

[38] On 31 August 2010, the final day of the summer transfer window, Pennant agreed a four-month loan deal with Premier League side Stoke City.

[40] Manager Tony Pulis indicated he would look to make Pennant's loan switch permanent in the January transfer window.

[54] Pennant went on to have an up-and-down season as he played in 40 of the club's 59 fixtures (starting in 23), helping the side reach the round of 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.

[57] However, with the arrival of Wolverhampton Wanderers winger Michael Kightly, Pennant was unable to force his way back into Tony Pulis' plans, and on 12 October 2012, he moved to Wolves on an emergency three-month loan deal.

[58] 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.

[citation needed] Pennant returned to England and joined Championship club Wigan Athletic on 21 February 2015 until the end of the season on a free transfer.

[77][78] On 28 December 2017, Pennant left Billericay Town, after just four months,[79] having made 13 appearances league (1 goal)[80] and 2 in the FA Cup.

[82] While on the England under-21 team, Pennant was sent home by head coach David Platt for breaking a curfew before an important match against Turkey.

"[85] Pennant is one of only two English players to have played in a UEFA Champions League Final, but never to have represented England at senior level, the other being Jamie Gittens.

[89] On 23 January 2005, he was arrested and again charged with drink-driving, and driving while uninsured, after crashing his Mercedes into a lamp-post in Aylesbury while still serving the ban for the first offence.

[90] He was released on parole after 30 days and immediately returned to playing for Birmingham City, although he had to wear an electronic tag at all times, including while on the pitch.

[92] 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.

Following a domestic disturbance in July 2007, he 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.

[95] According to Grove, she ended the relationship[citation needed] upon finding CCTV footage of Pennant cheating,[96] and "took revenge by destroying £200,000 of his designer gear".

[citation needed] In December 2008, Pennant's front gates at his home in Cheshire were ram-raided by burglars in an attempted robbery.

[105] For Season Two of the Apple TV series Ted Lasso, assistant director Sophie Worger hired former professional player Kasali Casal to manage the soccer choreography.