It’s hard to complain when you receive something for free but it would be difficult to criticise anyone for thinking that these free transfers were a waste of money.

Through a combination of injuries, bad luck or simply not making the grade, it’s hard to find any real positive in some of the signings Wenger has made through the free transfer market.

With that in mind, let’s relive those hellish moments when Wenger was pictured with a signing for free:


1. Arturo Lupoli

Lupoli, the young Italian striker from Brescia, was hot property when Arsenal signed him in 2004 from his maiden club Parma.

At youth level, Lupoli was prolific, scoring two goals per game at under-17 level. He was a potent finisher who excelled inside the box. At the end of his contract with Parma, he refused to sign an extension allowing Arsenal to swoop in and claim the treasured teenager.

The Italian striker continued his development where he left off at Parma, scoring prolifically for Arsenal’s youth. He struck up a strong partnership with Nicklas Bentdner and gained commendation for his performances in the League Cup in the 2005-06 season.

However, Lupoli struggled to maintain his high level of performance and left on loan to Derby. Despite a lack of goals at Championship level, Lupoli earned himself a permanent deal at Fiorentina at the end of his Arsenal contract.

Although there was promise the whole way throughout his Arsenal career, the youngster failed to make the step up to the senior level. Whilst there have been many transfers in the past that I think Wenger may have regretted, I believe this one was always worth a punt.