Arsenal boss Arsene Wenger revealed that missing out on Cristiano Ronaldo's signature in 2003 is the biggest regret of his career.
Before the Portuguese star, who was 18 at the time, went on to complete a £12.3 million switch from Sporting Lisbon to Manchester United in the summer of 2003, Arsenal had a chance to sign him.
However, Sir Alex Ferguson beat Wenger to Ronaldo's signature and the Portuguese went on to establish himself as one of the best players in the world, helping United lift eight major trophies in six years, before joining Real Madrid for £80 million (the world record transfer fee back then) in 2009.
The 29-year-old forward, who won the Ballon d'Or award last year, has gone on to become even more clinical at Real Madrid, scoring 257 goals in 252 appearances for the Spanish giants in all competitions.
And Wenger says that he rues not taking the opportunity to secure the Portuguese's signature in 2003.
"My biggest regret: I was so close to signing Cristiano Ronaldo. And not only did I not get him, but he signed for Manchester United. That, of course, still hurts today," said Wenger, while talking at Huawei's (one of Arsenal's sponsors) question and answer session on Thursday.
Apart from Ronaldo, the Frenchman also revealed how he narrowly missed out on Chelsea striker Didier Drogba's signature, when the Ivorian was a relatively unknown player at Le Mans.
The 36-year-old striker, who has re-signed with Chelsea following brief spells with Shanghai Shenhua and Galatasaray, also went on to establish himself as one of the most prolific strikers in the Premier League after completing a £24 million switch from Marseille to Stamford Bridge in the summer of 2004.
And Wenger says that he would have loved to manage Drogba, who scored against Arsenal in so many important fixtures.
"I would have loved to have managed Didier Drogba, for two reasons," said Wenger.
"One, I missed him when he played at Le Mans in France, not even in the top league. I knew there was a good player there and I missed him.
"And secondly, because he hurt us so much in big games that all this pain would not have happened."