Pennant did have a spell in Spain with Real Zaragoza, but revealed before then he had the chance to join Madrid.
"Real Madrid wanted to sign me when [ex-Spurs manager] Juande Ramos, was in charge there. 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," he told FourFourTwo magazine.
With Pennant discarded, Madrid brought in Julien Faubert on loan from West Ham just two days before the January 2009 transfer window closed. The French winger only played two games before his loan deal a few months later while Pennant was offloaded to Portsmouth.