#2 Simao Sabrosa
Figo was not the only Portuguese winger Liverpool failed to sign in the summer of 2005 despite being defending European Champions.
Simao was at Benfica in 2005 and at that point, he had scored 66 goals in 153 games for the club and was one of the best wingers in the world.
The move was very close to completion as the player was given permission to leave the Portuguese camp to fly to Liverpool to complete his medical. However, Benfica was not keen on losing their captain and raised their asking price to £13.6million and Liverpool was not willing to pay more than £12.3 million.
Interestingly, when Liverpool signed Fernando Torres from Atletico Madrid in 2007, Atletico Madrid replaced the Spaniard with Simao!