6. Euro 2004
Before the 2006 World Cup, England already had practice losing to Portugal in penalty shootouts as they had already met each other in the quarter-final stage of Euro 2004. After leading, England just let the whole game go to hell. Rooney suffered a broken foot and had to be taken off (he had already scored four goals in the tournament) and his replacement, Darius Vassell was nowhere up to the mark. After conceding their lead, the match ended 2-2 after extra time and England lost famously to Portugal in shootouts.
England was defensively ineffective during most of the game and their penalty takers were a huge disappointment. Their embarrassment was sealed when the winning penalty was taken by the Portuguese goalkeeper Ricardo.