England's 5 most painful World Cup exits

#1: World Cup 1990

In the nine World Cup tournaments they’ve played since their 1966 victory, the closest England have come to recapturing that glory was at World Cup 1990 in Italy.

That edition saw them reach the semi-finals, where they lost to West Germany, but the nature of the loss, coupled with the overall performance in the tournament, makes it by far England’s most painful exit.

Bobby Robson’s team had started characteristically slowly in the tournament, drawing their first two group stage games with the Republic of Ireland and the Netherlands.

But things started to pick up when a 1-0 victory over Egypt, sent them into the round of 16, and there, a last-gasp goal from David Platt at the end of extra time was enough to send them past Belgium and into the quarters.

The quarter-finals saw them almost upset by an unheralded, but brilliant Cameroon side inspired by 38-year old forward Roger Milla.

The African side went 2-1 up midway through the second half, but two penalties by Gary Lineker turned the tide and sent England into the semi-finals.

By that point, the likes of Platt, Paul Gascoigne, and Gary Lineker had begun to be seen as iconic superstars by the fans, and it looked like England finally had a side that could match up to the heroes of 1966.

The Semi-Final against old rivals West Germany in Turin is still spoken about in awe today. It turned out to be a classic match between two excellent and evenly-matched teams, and after 120 minutes, the score ended up locked at 1-1 with nothing to separate the two.

Penalty kicks were required, England’s first shootout in a tournament, and for the first, but not the last time, the Three Lions saw their hopes go up in smoke as Stuart Pearce and Chris Waddle both missed their kicks, sending West Germany onwards into the final.

Perhaps only Euro 1996 matches this effort in terms of painful losses for England, as they were literally inches away from the final and probably would’ve beaten a poor Argentina side had they gotten there.

Eighteen years on, it remains the closest England have come to repeating their 1966 feat, and that’s why it still remains painful for England fans today.