Jermaine Pennant, HMP Woodhill, 31 days
Jermaine Pennant was the most expensive teenager in Britain when he left Notts County to join Arsenal for £2 million in 1999. However he failed to live up to the price tag recieved numerous cautions and had his license suspended for driving offences. In 2005 he crashed his car into a lamp-post in Aylesbury and was sentenced to five months in prison. He was released after a month and became the first Premiership footballer to play with an electronic tag.