The Scot, born in Glasgow, moved to Italy with his family as a child and later joined Atalanta's youth squad.

He returned to Britain for a trial with Arsenal, who took him on but never played him in a first team match, before moving to Bournemouth 10 years ago from where Pompey bought him for £50,000 in 2002.

Now the 29-year-old is looking forward to the visit of Carlo Ancelotti's side on November 27.

"It's an absolutely incredible draw, something a footballer can usually only dream about but Milan are my team, their stadium is my Mecca," he said.

"I have watched them hundreds of times over the years. Their posters were all over my bedroom walls when I was a youngster.

"My oldest brother Patrick has a season ticket for the San Siro. I have so many friends who watch them and now, hopefully, I am going to be playing against them.

"Just think of it, wonderful players like Paolo Maldini, Kaka, Andrea Pirlo, Alessandro Nesta and Andriy Shevchenko are going to be coming to Fratton Park to play in the UEFA Cup. You couldn't make it up.

"It will be a fantastic occasion for all of us when we meet them - but for me it means the world."