The start of December marked not only the busiest month of the Premier League season, but also the draw for the 2018 World Cup. England have been drawn into Group G along with Belgium, Panama and Tunisia. They will likely compete with Belgium to top the group and advance to the knockout stages.

The Five Biggest English Disappointments of the 2000’s

Russia 2018 will mark a changing of the guard for the English. The squad will predominantly be filled with young, exciting prospects rather than the ageing “Golden Generation.” In typical English fashion, this young crop of talent will certainly garner some lofty expectations – which they will inevitably fail to live up to. In preparation for being underwhelmed, these are the five biggest English disappointments of the 2000’s.

5. Penalty Shootouts

The penalty shootout, the bane of England’s existence. The Three Lions have managed to be eliminated from major tournaments three times since the turn of the century alone.

England took on eventual runners-up Portugal in the quarter-finals of Euro 2004. When Frank Lampard nullified a Rui Costa stunner in extra time, spot kicks were fated to happen. All was square at five goals heading into the seventh round. Portuguese keeper Ricardo read Darius Vassell like a book before stepping up himself to crush English hopes.

Portugal was once again the opponent two years later at the 2006 World Cup – the day of Cristiano Ronaldo‘s infamous wink. When Wayne Rooney saw red in the 62nd minute England set up shop for the remainder of the match, doing well to get into the shootout. Canadian-born Owen Hargreaves was the only English scorer from the spot, with Ronaldo scoring the winner for Portugal – a last dash of salt in the wound.

Italy was the opposition in Euro 2012. Another match against eventual runners-up of a major tournament. England surprisingly managed to take a 2-1 lead in penalties after Riccardo Montolivo shot wide. Unfortunately Ashley Young and Ashley Cole proceeded to miss terribly, allowing the Azzurri to progress.

4. 2014 World Cup

While England were never expected to make a splash at the 2014 World Cup in Brazil, they failed to even cause a ripple. They were unlucky to draw into the group of death with Italy, Uruguay and Costa Rica. Yet Italy were ageing fast and Uruguay’s Luis Suarez was suspended for the first game of the tournament; England should have advanced.

In the final game of the group, England needed to beat group leading Costa Rica to have any chance of progressing. Yet manager Roy Hodgson decided to completely rotate the starting XI. The Three Lions played out a listless 0-0 draw and went home with their tails between their legs, finishing fourth in the group.

3. 2010 World Cup

English fans will always remember South Africa for Frank Lampard’s goal that never was against Germany. However, this isn’t enough to excuse England’s horrific performance in the group stage.

The Three Lions were by far the best team in their group which also held the United States, Algeria and Slovenia. They only managed to score two goals over the group stage, ultimately finishing second. Rob Green‘s horrific error against the Americans cost him his starting job, as well as two points that would have seen England win the group.

Had England topped the group, they would have met Ghana, rather than Germany, in the round of 16. They would have fancied their chances against the African side. A quarter-final date with Uruguay could have been a real chance at reaching the final four of a major tournament for the first time since Euro 1996.

2. Euro 2016

The Iceland debacle; often described as the worst performance an England side has ever had. In reality, losing to minnows Iceland was just the cherry on top of a tournament full of disappointment.

A last-minute Russian equalizer to begin the tournament foreshadowed the disasters to come. Beating British rivals Wales in dramatic fashion gave England hope of winning the group. However, Roy Hodgson inexplicably decided once again to rest star players, tying Slovakia and finishing second in the group.

While drawing Iceland was favourable, England would have then gone on to face hosts France. Had they miraculously beaten France, reigning World Cup champions Germany were waiting in the wings. Alternatively, had England won the group, they would have entered the less intimidating side of the bracket. They, along with Belgium and eventual champions Portugal, would have been favourites to reach the finals.

1. Euro 2008

The recency bias would indicate that being eliminated by Iceland is the biggest embarrassment the English National Team has suffered. However, just eight years earlier, the Golden Generation was humiliating the nation on a completely different scale by not even qualifying for a major tournament.

England dropped points in goalless draws against both Israel and Macedonia over the qualifying campaign. A loss to Russia in the penultimate qualifying match left England needing at least a point against Croatia to progress to the European Championships. The Three Lions began the match in typical English style by promptly conceding two goals in the first 15 minutes. A Frank Lampard penalty and Peter Crouch tap in drew England level and into the Euros. But ultimately a draw was too much to ask, as Croatia needed just 12 minutes to regain their advantage for good, eliminating all the Three Lions from contention.

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