5) Roberto Soldado (Valencia to Tottenham – £26m)
Spurs looked to the Spanish striker for goals following the departure of Gareth Bale in 2013. He had been a prolific scorer for Valencia in his three seasons at the Mestalla but it didn’t translate to English football.
Soldado scored just six league goals during his first season at White Hart Lane, with only two of them coming from open play. He spent one more campaign with the club before being sold back to Spain for a loss.