The Spaniard had a tempestuous relationship with Mourinho during his days as Liverpool manager, masterminding two Champions League semi-final wins over the Blues, including in 2005 when Luis Garcia took the Merseyside outfit to Istanbul with what Mourinho described as a "ghost" goal.
But, following his Real Madrid's 1-1 draw at Manchester City, Mourinho put his differences with Benitez to one side, and said: "I like my old clubs to win. I always wish the managers of my former clubs well so I always wish good luck to managers of my former clubs. I wish good luck to Benitez."
Di Matteo became the sixth Chelsea manager to lose his job since Mourinho's exit in 2007, paying the price for a bad recent run of results that has left the Blues' Champions League hopes hanging by a thread.
But Mourinho takes no pleasure from Di Matteo's misfortune.
"I am never happy when a manager is sacked," he said.
"It can happen to me so I never enjoy it. I always feel sorry for him and his family.
"Our lives are very similar. I am not happy with any situation."