Hughes was brought up in Milan.
And he will fulfil his lifelong ambition when the legendary Rossoneri visit Fratton Park in the UEFA Cup tomorrow night.
Milan fan Hughes, 29, whose dad Kevin was an accountant over there, said: "I know the old cliché is a dream come true, but this genuinely is.
"I had posters of Van Basten, Gullit, Rijkaard, Baresi - but Paolo Maldini was the one. I wanted to be like him and play like him.
"Even growing up in Atalanta's youth team I played left-back.
"Maldini was a constant in my childhood. He was always in that Milan side. I'd watch him in the San Siro and he'd be magnificent.
"He has to be one of the greatest players of all time."
Hughes, whose elder brother Patrick is a season-ticket holder at the San Siro, will get the chance to face his boyhood heroes because Lassana Diarra is sidelined by an ankle injury.
He added: "Patrick is over for the game and even had the cheek to ask me if I could get him tickets for the Milan end, which didn't go down too well.
"At least my other two brothers and my mum and dad will be supporting Pompey.
"I would have preferred the game to be away because the San Siro is my Mecca."