8. Jermaine Pennant
Crime: Drink driving while banned.
Jail Time: 30 days
Occurred in: 2005
Jermaine Pennant was a fairly quiet footballer, but in 2005, he was questioned by the police after crashing his Mercedes into a lamppost. He was driving at a speed which was twice the drink-drive limit. Interestingly, the winger presented himself as Ashley Cole to the police, for which, he was convicted and had to serve 30 days of prison. Also, it is interesting to know that Pennant has scored lesser goals than the number of days he spent on prison. He comes at the 8th spot in our countdown.