England's 5 most painful World Cup exits

England's 1990 loss to West Germany remains painful today
England's 1990 loss to West Germany remains painful today

#4: World Cup 1998

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England have been eliminated from the World Cup via a penalty shootout three times. We’ll look at the first time on a later slide, but of the remaining two (in 1998 and 2006), it’s the former that sticks out as being a harder pill to swallow.

In that instance, Glenn Hoddle’s side were eliminated by bitter rivals Argentina in the round of 16, after a truly titanic struggle that realistically should’ve gone England’s way.

Both sides exchanged penalties early in the first half, before teenage striker Michael Owen, scored a career-defining goal that was worthy of winning any World Cup tie. But a cleverly-worked free kick routine allowed Argentina to equalise on the stroke of half-time.

At 2-2 the game stood on a knife edge, but it seemed that the South Americans would have the advantage when David Beckham was sent off, after lashing out at Diego Simeone following a poor tackle from the Argentine midfielder.

As it turned out that wasn’t the case. England continued to battle on with ten men, and should’ve won the game when defender Sol Campbell headed home from a corner late in the second half.

But the referee disallowed the goal, feeling Alan Shearer had impeded goalkeeper Carlos Roa.

In the end, extra time could not separate the sides and penalties were required. This time the fall guys were midfielders Paul Ince and David Batty, who missed the crucial fifth kick, allowing Argentina to advance.

This was an incredibly painful exit for England as they had never really been second-best in the game, even with ten men, and had Campbell’s goal stood they would’ve advanced and from there, anything would’ve been possible.

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