Unfortunately, after the 2-1 defeat against the Italian giants, things went downhill for Pennant at Anfield, as he struggled for playing time the following season and was eventually shipped off to Portsmouth on loan before Liverpool ultimately released him in the summer of 2009.
Madrid expressed an interest in signing Pennant, but Ramos was unhappy at the prospect of the deal and the plug was pulled on a transfer to the Santiago Bernabeu.
“Real Madrid wanted to sign me when [the former Spurs manager] Juande Ramos, was in charge there," Pennant told Four Four Two magazine . "The board wanted to do the deal as they wanted a right winger.
“On transfer deadline day I got a call from my agent, saying, ‘You could be going to Madrid – keep your phone on'. But the board had gone over the manager’s head, so he started to get upset, and to placate him they pulled the plug on the deal.
"The club wanted me; the manager didn’t.”
The enigmatic attacker secured a move to Spain after leaving Liverpool, with Real Zaragoza, but he struggled to adapt to life in La Liga and was ultimately sold to Stoke City permanently in 2010 after a brief loan spell with the then-Premier League outfit.
Pennant went on to recall his time with Zaragoza , admitting he struggled to acclimatise to his new life abroad.
"The football was good," he added. "I loved how technical all the teams were, even the ones down at the bottom. The weather was nice.
"The pitches were immaculate. But Zaragoza was a bit difficult to live in as it was traditional Spain – it wasn’t very multicultural.
"On days off, I would go to Madrid or Barcelona for a good time. Once, I went to Barcelona for a night out and then got the train back on the morning of training, but I felt so bad that I couldn’t go in, so I told them I wasn’t well. The club doctor came to my house to check on me, but I didn’t answer the door. I think they knew!"