Di Matteo has risked embarrassing the Chelsea manager Andre Villas-Boas, who is one of the few managers not to have played the game professionally, with his comments.
The former Chelsea midfielder was asked if a management career would be aided by having played at the highest level.
"It helps because you understand the emotions, the stress that the players have because you went through that yourself," said Di Matteo.
"So it does help being able to deal with certain situations with the pressure.
"You naturally find yourself in an environment you've been in before."
Chelsea face Portsmouth in today's FA Cup third round.