I left Arsenal because things were going nowhere - I loved my time at Liverpool

The former Arsenal star found a new lease of life when he moved to Anfield

Ex-Arsenal winger Jermaine Pennant once claimed he left the Gunners as he was "going nowhere" at the club. Pennant, who retired from the game in 2017, moved to Birmingham City after leaving north London.

However, he later signed for Liverpool, his boyhood club, a moment he said was "the best feeling in my life". Pennant, 42, had a chequered career in the game, experiencing some major highs and dramatic lows.

The winger became the most expensive teenage footballer in Britain when Arsenal bought him from Notts County for £2million when he was just a 15-year-old. His rollercoaster career even took him to the Champions League final with Liverpool where he faced Milan at the Olympic Stadium in Athens in 2007.

He also played across England, Spain, India and Singapore. But it's perhaps Pennant's time at Arsenal and Liverpool, with his two former clubs meeting in the Premier League on Thursday evening, that lives longest in the memory.

Speaking of signing for Arsenal, he told William Hill in 2023 of the sheer ecstasy he felt of getting to rub shoulders with several club icons.

"I remember when I was 15-years-old. I was in the digs at Notts County and I got a knock on my door. It was an agent and my dad," Pennant began. "He said ‘son we’re off to London, you’re about to sign for Arsenal’. I remember saying ‘are we? I don’t get a say in the matter!’

"It was amazing seeing such legends walking around. [Thierry] Henry, [Tony] Adams, [Nicholas] Anelka – this was my dream coming true but it was overwhelming," he said. "My life changed. I was recognised, I was quite well known and my name was in the press. Being that age you don’t realise what it means, as a kid you still do your things and you’re still immature."

Pennant appeared to have achieved lift-off in his Arsenal career when he bagged a superb hat-trick, on his debut, in a 6-1 win against Southampton in May 2003. Yet he was swiftly benched again for the following game and, ultimately, only managed 12 appearances for Arsenal during the six years he was at the Gunners.

Speaking to The Guardian in 2017 he said: "After the hat-trick I was on the bench the next game. I thought that was the start of it and I would just kick on at Arsenal. But it never happened and I got more and more frustrated and lost interest. I thought: ‘This is going nowhere'".

Pennant made 81 appearances at Liverpool after signing for the Reds on a four-year contract for £6.7m in July 2006. While he never hit the heights at the Reds, he waxed lyrical about signing for the club he had supported all his life.

Elaborating to William Hill he said: "I had two really surreal moments in my career. There’s clearly playing in the Champions League final, that is every pro players’ dream.

"Then the news that I was signing for Liverpool, a moment I will never forget. I had just come out of prison [For a drink driving conviction] playing for Birmingham, then a year later my agent calls and says we’re signing for Liverpool. To come from that, to sign for the club I supported as a kid, was one of the best feelings in my life.

However, he told The Guardian that injuries where responsible for his brief time at the club. “The first season I did well," he said in 2017.

"Liverpool were also the team I supported as a boy. So it was great. The turning point with Rafa [Benitez] came when I got injured. After that I struggled to get back in the team."