By Mark Bennett at the Jan Breydelstadion
Kaka's 86th-minute volley took AC Milan to the top of UEFA Champions League Group H - but for much of the game it seemed the holders were set to end the day at the opposite end of the tight pool.
Club Brugge KV suggested for long periods that they could repeat their shock at the San Siro, especially after Alessandro Nesta's first-half sending-off. But they could not take advantage of their extra man, leaving Kaka to strike a superb winner.
As expected, Brugge coach Trond Sollied fielded a defensive 3-5-2 lineup in front of goalkeeper Dany Verlinden, who passed a late fitness test this morning. Milan coach Carlo Ancelotti chose a slightly more attacking 4-4-2 system with Jon Dahl Tomasson replacing the injured Filippo Inzaghi alongside Andriy Shevchenko, and Kaka playing directly behind the two strikers.
Only a few seconds into the match the roles became clear. Milan tried to put pressure on Brugge, whereas the Belgian side searched for chances on the break and came close when Gert Verheyen shot wide with only 30 seconds gone. In the following 20 minutes Milan looked the better side, but never troubled the tight Brugge defence.
At this stage of the game neither goalkeeper had been involved - but that changed after 22 minutes when Verlinden was called upon for the first time. Gennaro Gattuso slipped three challenges and tested the veteran custodian from just outside the area, but the former Belgian international collected the ball comfortably.
After 34 minutes Milan were forced to make an early replacement when captain Paolo Maldini limped off the field and was replaced by Alessandro Costacurta. Only three minutes later Milan's defence was depleted further when German referee Herbert Fandel dismissed Nesta for a second bookable offence after the central defender brought Andrés Mendoza down in midfield. Ancelotti made his second change soon afterwards to compensate for Nesta's loss and replaced Tomasson with Dario Šimic.
Mendoza hits the bar
Early in the second half the run of play changed. With Milan down to ten men Brugge were more willing to get players forward. That nearly paid of in the 54th minute when Mendoza's header rebounded off the bar following a cross from Ivan Gvozdenovic. Soon after, the Peruvian striker made a good run into the penalty area but Dida hung on to his shot.
Stoica sent on
Sollied then sent Alin Stoica on in place of Nastja Ceh, obviously hoping that the Romanian would come up with the necessary ideas to break down Milan's defence. Only two minutes later Brugge came close once again when Mendoza's attempt was cleared at the last second for a corner. At this stage, Brugge were in complete control.
However, they could not take advantage, even when striker Bengt Sæternes was brought on 14 minutes from time. Dida was forced to make a great diving save to deny Stoica four minutes later, but then the Italian side struck with their first real chance of the second half when Kaka applied a perfect finish to a cross from Cafu. From possibly ending the day bottom of the group - albeit only a point behind leaders AFC Ajax - Milan now sit top. Brugge, meanwhile, are down in fourth.