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Christian Panucci took advantage of some unusually slack Chelsea defending to finish off a Cicinho cross.
BBC: Roma 3-1 Chelsea
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Panucci missed from two yards from a Pirlo free-kick as Italy threatened on the break.
BBC: Scotland 1-2 Italy
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Italy coach Roberto Donadoni had chosen Panucci ahead of Massimo Oddo at right-back and Gianluca Zambrotta instead of Fabio Grosso on the left.
BBC: Scotland 1-2 Italy
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But Ferguson forced the ball home when Lee McCulloch's effort was saved after 65 minutes only for Panucci to head home from a disputed Pirlo free kick.
BBC: Scotland 1-2 Italy
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Worse was to follow when the free-kick was played to Cicinho down the right and his centre found Panucci, who was left free to glance the ball home.
BBC: Roma 3-1 Chelsea