1. Fernando Torres (Liverpool to Chelsea)- £50 million
El Nino tops the list as the most expensive winter transfer. The mammoth deadline day deal would not be forgotten by anyone at Liverpool or Chelsea. The Spanish striker was running riot around Premier league defenses during his time with Liverpool and Chelsea were in his pursuit for a long time. With bids being turned down, Chelsea came up with the huge price for the striker which eventually saw him sign for the London club. But that move started the landslide for Torres who never matched his form at Liverpool. And along with that came a stream of fitness problems which further deepened his concerns. He scored just a single goal in his first half season and went onto be remembered for shocking misses.