Manchester United striker Alan Smith missed a spot kick in the shoot-out as Bayern Munich beat the English premier league side 4-2 on penalties in the second match of the Champions World Series in Chicago on Sunday.
A crowd of 58,121 packed into Soldier Field to watch a disappointing friendly end in a scoreless draw before the contest was decided by a shoot-out.
Smith, making his debut after a seven million pound ($12.8 million) move from Leeds United in May, and Republic of Ireland defender John O'Shea failed from the spot as a more experienced Bayern side converted all of their penalties.
The match was the German side's only contest in the series, which continues on Monday with Scotland's Celtic taking on England's Liverpool in Hartford, Connecticut.
Manchester United's next game is against Celtic in Philadelphia on Wednesday.
Chelsea opened the series with a 4-2 victory over Celtic in Seattle on Saturday.
