Italy 0-0 Holland (AET, 3-1 penalties), 2000 semi-final
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This match was perhaps the most exciting 0-0 draw ever—a proof that great matches are not only about late winners or Istanbul-esque comebacks. This was the golden era of football when the field was filled with too many legends, the likes of Paolo Maldini, Fabio Cannavaro, Filippo Inzaghi, Alessandro Nesta from the Italian side and Edwin van der Sar, Frank de Boer and Dennis Bergkamp leading the Dutch side.
In this Amsterdam semi-final, Italy were already reduced to 10 men when Gianluca Zambrotta was sent off in the 34th minute and gave away a penalty. Dutch captain Frank de Boer stepped up but his shot was saved by Francesco Toldo.
At the hour mark, Holland were again awarded a spot-kick, and this time, it was Patrick Kluivert’s chance to miss, hitting the post from 12 yards out. Italy somehow hung on and the tie drifted into extra time but could not be settled through a Golden Goal. And then, it was time for the infamous penalty-shootout.
Luigi di Biagio scored Italy’s first spot-kick and for the second time in the night, De Boer walked to the penalty spot to take his, but you could just feel that it wasn’t going to be Holland’s day as the legendary Dutch captain missed the penalty again.
Italy dispatched their first three penalties, and Holland missed three out of their four kicks to end the tie 3-1 in favour of the Azzurri. The Dutch were eliminated on penalties for the fourth time in five major tournaments as Italy advanced to a UEFA EURO 2000 final against France.
