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Ronaldinho's saved penalty proved very costly indeed, as Palermo ran riot in a 3-1 victory that leaves Milan six points adrift of Inter.
The Rossoneri have been stuttering recently, notching up two last-gasp 2-2 draws on the trot away to Torino and Portsmouth to widen the gap from leaders Inter to three points. Last season they fell 2-1 in Sicily and made the trip this time without Marco Borriello, Alessandro Nesta, Gennaro Gattuso and the suspended Kaka. Palermo had no injury problems, but had won just one of their last seven Serie A games.
Fabrizio Miccoli went to charge into the box, but was winded by Daniele Bonera's obstruction, although the referee waved play on. Moris Carrozzieri's glancing header from a Miccoli free kick skimmed the upright, but Bonera's volley on Ronaldinho's cross was deflected wide.
Alexandre Pato's glancing header whistled past the far post, but the young Brazilian had a great chance on 17 minutes. A terrible defensive intervention from Antonio Nocerino was basically a backpass to Pato, but Marco Amelia did well to parry from point-blank range.
Just 20 seconds later Miccoli's fierce snapshot from 30 metres was palmed out of the near bottom corner by Christian Abbiati. From the resulting corner Massimo Ambrosini performed a goalline clearance to deny Miccoli again!
Abbiati got down brilliantly again to keep out Miccoli's daisy-cutter volley from the edge of the box.
Pato was off for treatment after a knock to the ribcage, but soon after coming back on, Amelia clattered into him as he sprung the offside trap and the referee pointed to the spot. The contact was right on the edge of the box and difficult to tell whether it was inside or out. Ronaldinho stepped up and took a very long curved run-up, but Amelia guessed the right angle and palmed it out of the far corner! It was a fine save, as the ball was heading right into the bottom corner.
Pato did not recover from that knock and made way for Fratton Park hero Pippo Inzaghi.
Mark Bresciano's fresh-air shot was a relief for the chaotic Rossoneri defence, then Fabio Simplicio rolled through for Miccoli to burst into the box, but Marek Jankulovski performed a crucial tackle as he was pulling the trigger from eight yards.
The Rosanero were pinning Milan back into their own final third in the last 10 minutes of the first half, but could not find a way through. Inzaghi was tripped by Cesare Bovo and this time it was inches outside the box. With the final kick of the first half, Ronaldinho curled that free kick on to the crossbar!
Five minutes after the restart, Miccoli finally won his personal duel with Miccoli. The 'Pocket Striker' went on a trademark run, cut back in from the left and when he saw a gap between defenders unleashed a rocket measured at 106km/h that flashed into the far bottom corner.
Carlo Ancelotti threw on Andriy Shevchenko and Emerson, moving Ronaldinho behind the two strikers. Almost immediately Clarence Seedorf's effort hit Inzaghi and the ball ricocheted into Sheva's path for a fine Amelia save.
Moments later Palermo doubled their advantage with Edison Cavani redirecting Fabio Liverani's cross into a looping header from the penalty spot. The Uruguayan out-jumped Paolo Maldini and twisted in the air.
This was the second time Milan had found themselves 2-0 down in four days, as they fought back to draw 2-2 in stoppages at Portsmouth on Thursday evening. Zambrotta chested down a long ball for Ronaldinho, who shinned his volley.
Mattia Cassani charged down Jankulovski's blockbuster, then Amelia flew to palm an Andrea Pirlo free kick out of the bottom near corner. The tension was getting to Ancelotti, who broke the rules by smoking on the touchline.
Abbiati's palms were stung by a Simplicio screamer, then Sheva exchanged passes with Seedorf to spring the offside trap and Amelia bravely smothered at the Ukrainian's feet.
The hopes of a comeback were wrecked 10 minutes from time when Simplicio was left unmarked for a free header from six yards Federico Balzaretti's cross from the left. The Brazilian was given all the time in the world to line up his finish.
Ronaldinho didn't give in and went on a blazing run through a crowd of Palermo shirts until he was clearly tripped by Bovo. The former Barcelona man decided to take it again after the save in the first half and, although Amelia got the angle right again, this time slipped the ball under his arm.
Dinho was leading the improbable charge now and Carrozzieri blocked another run in the box with a clean tackle, then he blasted just over from 25 metres. Amelia had his palms stung by a Zambrotta half-volley that was heading under the bar from a very tight angle and repeated the trick on Emerson.
It was too little, too late from Milan, who seemed to compress their entire performance into the last 10 minutes. Amelia performed another very tough save on Pirlo's daisy-cutter in stoppages. Substitute Succi nearly got a fourth on the counter, but Bonera timed his sliding tackle perfectly.
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