5. David Bentley
David Bentley began his football career as a graduate of the Arsenal Football Academy.
The midfielder, however, made only nine professional appearances for the Gunners before moving to Blackburn Rovers in 2005.
His career path brought him back to North London three years later, but this time, his destination was the White Hart Lane Stadium.
Bentley spent two seasons at Tottenham, netting five goals in 62 appearances – one of which was a true wonder goal against his former side Arsenal FC.