Failing to sign Cristiano Ronaldo is outgoing Arsenal manager Arsene Wenger’s biggest transfer regret in his almost 22-year-reign at the Premier League club, the 68-year-old has said.

Wenger signed some of the league’s best players during his reign, including Thierry Henry, Robert Pires, Cesc Fabregas and Mesut Ozil, but Arsenal lost out on signing Ronaldo to rivals Manchester United in 2003.

Ronaldo went on to help United win three league titles along with an FA Cup and Champions League triumph, before joining Real Madrid in 2009.

“The obvious player (that we missed out on) that comes to mind is (Cristiano) Ronaldo,” Wenger told Arsenal’s website https://www.arsenal.com.

“He was here with his mother and we were very close. Then Man United came in and they had Carlos Queiroz at the time, who was their coach. United played against Sporting Lisbon and Ronaldo was outstanding and they signed him.

“You could imagine at the time what it would have been like to have Thierry Henry and Ronaldo together… That would certainly have changed a little bit the history of my stay here as well.”

Wenger said the north London outfit were unable to compete with United’s 12 million pounds ($16.23 million) offer for the Portugal international.