9. Ashley Cole (Arsenal-Chelsea)
The reason this transfer has lived so long in the memory is all down to the tapping up scandal that surrounded it. Rumours had been going around that Ashley Cole had had a hotel meeting with people from Chelsea back in 2005 and in 2006
Cole was fined a record £100,000 for the incident whilst Chelsea manager Jose Mourinho was fined a massive £200,000. On top of all this Cole was also branded a Judas by Arsenal fans since Chelsea are not only Premier League rivals but also London rivals as well. Cole as had the last laugh though, having lifted numerous trophies in his time at Chelsea including the Champions League and the Europa League whilst Arsenal have not won a trophy in 8 seasons.