Classic Match: Juventus vs. Milan 1999/00

Alberto Zaccheroni’s Milan side swaggered into Turin for the tie of the round on match day ten of the 1999-00 Serie A season. Not only were the Rossoneri defending Champions, but they came into this clash undefeated in the previous nine rounds, comfortably seeing off Venezia 3-0 at San Siro before the trip to Turin.

Milan’s hosts, Juventus, were quietly going about their business though. Despite the surprise week four loss away at Lecce and the goalless draw in the Derby della Mole the week before the Milan clash, Carlo Ancelotti’s side sat a point ahead of their visitors for the game on 22 November 1999.

As the teams emerged, Antonio Conte had that distinctive stare locked on, proudly leading his team out; nothing could make him flinch, he meant business. As Carlo Ancelotti sat cool as a cucumber on the bench, his opposite number was taking in the spectacular scenes the fans were putting on inside the packed Delle Alpi. It had all the makings of a classic Italian match under the floodlights.

With both teams at full strength, Milan started the brighter, and it was no surprise when the champions took the lead inside the opening 20 minutes. Demetrio Albertini clipped a ball towards George Weah in the box, the Liberian effortlessly brought the ball under control immediately and, as he twisted and turned trying to get the better of Paolo Montero and Ciro Ferrara, sent a hopeful ball toward the back post. The ball flew over the head of Edwin Van der Sar and Milan defender Luigi Sala headed it towards goal only for the ball to come off the helpless Zinedine Zidane, putting the visitors in the lead.

As Zaccheroni flapped about on the touchline, Ancelotti remained the coolest man in the stadium, almost like he knew what was coming next.  Less than 60 seconds after Milan took the lead, Alessandro Del Piero whipped a wicked free kick in. Antonio Conte got the better of Albertini in the Milan box and the Juventus captain’s bullet header flew past the diving Christian Abbiati to square the game up.

Juventus boy wonder Del Piero was pulling the strings for the hosts on this cold November night—just four minutes into the second half he was the architect of Juve’s second goal. Running toward the heart of the Milan defence, he slipped a neat ball through to Filippo Inzaghi, who, under pressure from Paolo Maldini, didn’t even look or think where the goal was before hitting an incredible first-time effort across Abbiati. Despite the ‘keeper getting a hand to it, the ball found the net putting Ancelotti’s side 2-1 up.

Zaccheroni responded quickly. Off came Alessandro Costacurta followed by Gennaro Gattuso five minutes later, being replaced by the more attack minded Roberto Ayala and Seginho respectively. Leonardo was also thrown on in the latter stages as Milan desperately tried to get back in the game.

However, despite Milan’s best efforts, Juventus remained very much in control of the game and it would be a substitute of their own that would have the final say. With just four minutes to play Darko Kovacevic came on to replace hero of the hour Filippo Inzaghi.

Alessio Tacchinardi hooked an aimless high ball into the Milan penalty area as they game entered its final minute of stoppage time. Some indecision in the Milan penalty area allowed Kovacevic to get the better of Sala and loop a header over the struggling Abbiati, wrapping up all three points for Juve and putting them four points clear of Milan at an early stage of the season.

Milan travel to Turin once again this Friday night, and Max Allegri’s side will be out for revenge as Milan came out on top in the reverse fixture back in October through a Manuel Locatelli strike at San Siro. As for Milan, they’ll be hoping their hosts have one eye on Tuesday night’s Champions League clash with Porto as they look to do the double over Juventus.

Words by Giovanni Dougall @giovannid86

Gio has been part of the Gentleman Ultra team since 2013 and is the creator of @ClassicCalcio and @Solo_Parma. He regularly travels to Italy to follow his beloved Parma.