The Milanese knew all about Joe Jordan, the Tottenham Hotspur's assistant manager, before the first leg of the Champions League match. They had called the Scottish centre forward "Lo Squalo" (The Shark) when he played at San Siro in the early 1980s.
Jordan was Milan's only foreign player, having moved to Italy in 1981 after a successful career with the Uniteds of Manchester and Leeds in England.
"It was the best move in my career," he said. "Italian football, I quickly discovered, was hard and intense and beautiful at the same time. I learnt the language and loved the culture. I'd wanted to play abroad for some time after Leeds United refused to sell me to Bayern Munich some years earlier."
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Being a footballer in Italy was very different to England.
"It was a better way of living," Jordan said. "I'd come from a working-class background in Scotland and I was playing in a dressing room of Italians who all seemed well educated and cultured - it was difficult for me, but I loved the Italian culture, the cafes, restaurants and museums.
"Not that I had much time. There was no free time in Milan - your time is the club's time. You represent AC Milan at all times."
Jordan played in a side fill of Italian internationals who would go on to win the World Cup in 1982.
"Franco Baresi was a young lad at Milan and he told me that he could get me tickets for the World Cup final in Madrid," Jordan said. "I arrived in Madrid wearing a T-shirt and flip flops with Gordon McQueen, my best friend who I'd played with at Leeds and Manchester United."
Baresi and Jordan played for Milan during a time of serious upheavals following a bribery scandal which rocked Italian football a year before he arrived. Players were imprisoned, the club president lost his job and Milan were relegated to Serie B - though they were promoted for Jordan's arrival.
"I scored against hated rivals Inter in one of my first games which saw me mobbed by fans," he recalled.
"I thought it would be the start of an Italian dream, but results were not good for us."
"I lay flat on the team bus with my teammates when bricks were coming through the windows after a game that the referee had to dress as a policeman because his decisions had so inflamed the crowd," he said.
But Jordan grew to understand the Italian mentality. "Italy's a great country. I have a daughter who lives in Milan. The Italians have their ways, but as long as you know what they are like you are fine."
When he left Milan, Jordan stayed in Italy and moved to Hellas Verona, so enamoured was he of Italy, its football and its lifestyle. He still admires Milan as a football club.
"I didn't need to speak to the Tottenham players when the draw was made," he said. "Milan speak for themselves as a club. They've won more European Cups than any other team aside from Real Madrid.
"There are clubs in the world that are special like Madrid, Manchester United, Barcelona and AC Milan. These clubs have class and tradition. When I go back to Milan there are still people who work there from when I played there. I like that. When the draw was made I spoke to my old neighbours and we arranged to meet in Milan."
Jordan did have a word about the anticipated atmosphere, though. He understands the effect the passionate support given by Italian fans on special nights can have on even the most experienced players.
"I told them about the great arena of the San Siro, the size and the thunder of the crowd. Told them that it could be moving and inspiring at the time. I was important that our players were not daunted."
Jordan, after spells managing four other British football teams, has been at White Hart Lane since 2008, following Harry Redknapp when the manager moved from Portsmouth, where the pair worked together. He is satisfied with Tottenham's progress in their first Champions League campaign.
"We were naive in the early games in the Champions League, because it was all new to us," he said. "I think we've learnt quickly though and are well prepared for the biggest teams this season."
Tottenham's 1-0 victory in Italy proved that. It was just a shame that it was overshadowed by Jordan's spat with Gennaro Gattuso. The fiery midfielder was given a four-match ban for his butt on Jordan at the end of the match.
Much was written in the English press about Jordan's reputation and his once fearsome appearance on the pitch. Journalists reminisced nostalgically about the young Joe Jordan and how, in his prime, he would have seen off Gattuso.
Not that Jordan today is interested in any of this, only in fervently preaching the virtues of Italy and hoping Tottenham can acquit themselves as well as in the first leg.
Van der Vaart v Flamini
Van der Vaart, below, has not played since the first-leg victory in Milan after suffering a calf injury. However, he is set to return to the starting XI to orchestrate the Spurs attack. Flamini will have to contend with a hostile White Hart Lane crowd on his back as well as the attacking threat of the Dutchman.
Do Tottenham commit to attack to get the goal that could settle the tie or do they play in a more reserved style and wait for AC Milan to make a move? The Italians know they need to score so the first goal in this one will be pivotal.
Milan have never beaten Tottenham, though two of the previous meetings were back in 1972.
Tottenham (4-5-1) Gomes; Corluka, Dawson, Gallas, Assou-Ekotto; Jenas, Lennon, Modric, Pienaar, Van der Vaart; Crouch
AC Milan (4-4-2) Abbiati; Abate, Legrottaglie, Nesta, Jankulovski; Flamini, Seedorf, Thiago Silva, Robinho; Ibrahimovic, Pato.
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Martins of Benfica.