Chelsea got what they came for here last night. Gianluca Vialli had said he would be happy with a point and his team delivered. It took them a long way towards qualification for the second group stage of this competition.
Milan's unrelenting pressure in the second half was rewarded with a goal from the German striker Oliver Bierhoff. But Chelsea hit back immediately with the captain Dennis Wise scoring the equaliser.
The London side had entered San Siro's cacophonous cauldron determined not to be overawed by this most atmospheric of football stages.
Right from the first whistle they showed their confidence in the brave way they took the game to Milan, forcing the young Christian Abbiati to make two saves in the first seven minutes.
First Tore Andre Flo turned Roberto Ayala on the left of the area and unleashed a shot that Abbiati held at the second attempt. Then Wise and Flo set up Dan Petrescu on the right of the area and the goalkeeper saved the ensuing shot with his outstretched right leg.
Slowly but surely, however, Milan crept back into the game, shaking off Chelsea's early impertinence and creating a series of openings themselves, the first two from Chelsea errors.
In the 19th minute the Premiership side conceded a dangerously positioned free-kick that Andriy Shevchenko curled from 25 yards out just wide of the rooted Ed de Goey's post.
Five minutes later Celestine Babayaro stupidly gave the ball away, allowing Milan to manoeuvre the ball to Massimo Ambrosini 18 yards out. Thankfully for Chelsea, the quick-thinking Albert Ferrer dived in to block the goal-bound shot.
Milan went even closer a minute later when Shevchenko headed the ball against the outside of the post from Ambrosini's cross and Leonardo shot just wide shortly before half-time.
Milan also put together a series of attacks that did not reach De Goey thanks to desperate and lastditch interventions from Babayaro and Frank Leboeuf, who was regularly called into action as a makeshift sweeper.
Yet Abbiati was never able to rest, as Chelsea's persistence and clever running off the ball carved out a couple of dangerous openings at the other end, offering a timely reminder to Milan that Gianluca Vialli's side still posed a danger.
On 21 minutes a great ball from Petrescu found Wise on the right of the Milan area with space to uncork a cross that Flo, stretching at the back post, lifted just over the bar.
Just before the half-hour Albert Ferrer, pushing up into the right corner of the Milan area, went closer still, unleashing a shot that was heading for the top left of Abbiati's goal until the goalkeeper acrobatically tipped it away for a corner.
At half time Chelsea suffered something of a set-back when they were forced to substitute Petrescu, who had felt ill before the game. His departure forced Chelsea to switch Wise to the right wing and bring on Jody Morris to play in central midfield.
Milan quickly rejoined the hunt. Just eight minutes after the restart De Goey was forced to make a flying save from Ambrosini's 25-yard volley and four minutes later Bierhoff headed over from close range.
Chelsea were finding it difficult to break out of their half. One rare opportunity saw Wise cross from the right and Poyet's header force a reaction save from Abbiati.
Eventually Milan's pressure proved irresistible. On 75 minutes Wise allowed Serginho to put over a cross from the right that flew over Desailly at the near post and fell to Bierhoff, who had stolen a yard on Leboeuf. De Goey could only help the German's powerful header over the line.
Chelsea were down, but not out. A minute later Di Matteo fed Wise on the edge of the area. The Chelsea captain controlled the ball with his right foot and shot left-footed through the advancing goalkeeper's legs just inside the far post. It was the perfect response.
Gianluca Vialli heaped praise on his side, but warned Chelsea they must finish their European task next week.
Vialli said: "Dennis' goal was vital but it will be meaningless if we don't get a point against Berlin.
"If we go through Dennis, as the captain, will probably be the right person to have done it for us in the San Siro.
"He has had quite a difficult time in the last week because of the sending off at Liverpool but I think he deserved it tonight.
"I rate him as one of the key players in the team. Sometimes he makes mistakes and sometimes I am not happy with him but overall he is great for the team and that is why he's the captain.
"He doesn't score that many goals but he was playing wider in the second half because Dan Petrescu came off and he knew when we had the ball on the left side he was free to make runs forward coming inside or going outside.
"Roberto di Matteo played a great part in the goal. He won the ball back, looked up and his pass was spot on. Dennis controlled it very well and put the ball in for a goal to be proud of."
AC MILAN: Abbiati, Costacurta, Ayala, Maldini, Guly, Gattuso, Ambrosini, Leonardo (Boban 57), Serginho (Orlandini 86), Bierhoff, Shevchenko. Subs Not Used: Rossi, Helveg, De Ascentis, N'gotty, Sala. Booked: Ambrosini, Ayala, Leonardo, Costacurta. Goals: Bierhoff 74.
CHELSEA: De Goey, Ferrer, Desailly, Leboeuf, Babayaro, Petrescu (Morris 46), Deschamps, Wise, Poyet (Di Matteo 75), Zola (Ambrosetti 81), Flo. Subs Not Used: Cudicini, Hogh, Sutton, Lambourde. Booked: Zola, Ferrer. Goals: Wise 77.
Referee: N Levnikov (Russia).