Italy overcame Portugal on penalties to seal a berth at the 2008 Beijing Olympics, despite the sending off of Giuseppe Rossi.
The United striker received his marching orders in Nijmegen after collecting a second booking for dissent in the 74th minute.
Rossi had earlier come close to opening the scoring for the Azzurini, showing great pace to burst past three Portuguese defenders and into the area, but his powerful shot was superbly blocked by goalkeeper Paulo Ribeiro.
New United team-mate Nani also enjoyed an eventful game for the Portuguese, going close on two occasions to opening the scoring for the underdogs.
Nani did find the net eventually, in the subsequent penalty shootout after the match had finished 0-0, but misses from team-mates Manuel Fernandes and Antunes gifted Italy a 4-3 win and a berth in China.
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