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Tim Howard's return to his roots ended in disappointment for the Manchester United goalkeeper on Saturday.
The former MetroStars shot-stopper was the fall guy in an extraordinary penalty shoot-out. He saw his spot-kick come back off the post to hand Milan victory after they had equalised with only seven seconds to go.
Paul Scholes gave United the lead but they have ended their tour of the United States with three defeats, albeit two of them on penalties.
Scholes was at the heart of everything good about United's display in front of an astonishing crowd for a friendly - 74,511.
Certainly there was more urgency in their performance than in the two previous defeats on tour by Bayern Munich, on penalties, and Celtic.
Scholes and France defender Mikael Silvestre made their first starts of the tour.
Wales winger Ryan Giggs was also named in the team at the Giants Stadium along with Wes Brown, who has been troubled by an Achilles problem.
Andriy Shevchenko deflected in a free kick in the 90th minute as AC Milan went on to beat Manchester United 9-8 on penalties after a 1-1 draw in the Champions World Series.