The pressure is on manager Roy Hodgson and his players, who in the build-up have been reminded of some of England's most catastrophic nights.
However, England have also enjoyed some famous qualifying feats, and in the interests of balance it is only right that we also celebrate these ahead of the two matches at Wembley.
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World Cup 1990: Butcher bleeds for the cause
There have been fewer more arresting sights in the long history of English football than a blood-soaked Terry Butcher, wild-eyed and magnificent, helping his team secure a 0-0 draw in Sweden that took them to the brink of the World Cup finals of 1990 (a draw in their next game against Poland completed the job). It is an iconic shot which appeals to the cherished national stereotypes of a country that has traditionally revelled in blood and thunder football.
In these more health-conscious days, Butcher would have been ordered from the field of play until the flow of blood from a head wound was stemmed, but back in 1989, he was allowed to repeatedly head the ball away, reopening the gash and coating his sparkling white shirt in a deep shade of red. Butcher's sacrifice was worth it as England held Sweden to a 0-0 draw in a qualifying campaign which saw Bobby Robson's side fail to concede a single goal.
What happened next? English football changed forever. Gazza cried as England were knocked out in the World Cup semi-finals when losing on penalties to West Germany but the country had grown to love its national sport - demonised by politicians and tainted by hooligans - once again. Robson stepped down to take the PSV Eindhoven job as a national hero.
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World Cup 1998: Ince puts his head on the line
For Terry Butcher in 1989, read Paul Ince in 1997. This time it was the midfielder who found himself doused in blood as England went to Rome and claimed the draw they needed to progress to the World Cup finals in France as group winners. This was a monumental performance from a team that under Glenn Hoddle appeared to be maturing very nicely, and looked destined to make a big impact at international level.
Ince marshalled the midfield in a resolute performance while Ian Wright went close for England, striking the post in the second half. England fans almost had to turn away in horror when Christian Vieri was presented with an easy headed chance late on but the much-coveted striker contrived to put the ball over the bar. A certain Roy Hodgson was working as Hoddle's interpreter on the night, helping him tell the Italian press: "If we are capable of coming to a place like this and in a game of this nature, and getting the desired result when all the pressures are on you, and everything is conspiring against you, then it shows that you are capable of doing it when it comes to the finals next summer."
What happened next? England were eliminated in the second round of the 1998 World Cup in France, losing in penalties to Argentina after an epic encounter in St Etienne. David Beckham's kick at Diego Simeone caught the headlines but Michael Owen's stunning solo effort also singed itself on the memory. Hoddle lost his job in February 1999 after making distasteful comments about karma and the disabled.
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World Cup 2002: Beckham's masterpiece
Even 12 years on, the memory of David Beckham's greatest ever performance sends chills down the spine. This was quite simply a virtuoso solo display; Beckham not only covered every blade of grass, he seemed to make almost every tackle, every pass and take every shot. As his colleagues faltered badly - allowing Greece to take a 2-1 lead into injury time - Beckham, through force of personality and talent, simply refused to allow England to be pushed into a play-off.
With group rivals Germany beginning to celebrate their passage to the finals having drawn with Finland, England won a late free-kick. Beckham, the world's most effective practitioner of the set-piece art, sensed fate aligning in his favour. Thousands of hours of practice came to bear and once again Beckham displayed his uncanny ability to grasp the moment in front of him, bending his effort past the keeper with seconds remaining to ensure England went through automatically. "When you see Beckham score in the last minute, that's not luck, that's skill," said Sven-Goran Eriksson.
What happened next? Beckham's superstar status got a big bump, but England suffered major tournament disappointment again when ceding a lead to lose to Brazil in the quarter-finals in Japan and South Korea. The 10-man South Americans celebrated a ridiculous goal from Ronaldinho, leaving David Seaman looking silly.
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Euro 2004: Tension in Turkey
Beckham, as ever, was at the centre of things again on a fraught night in Istanbul in 2003. Away fans were banned due to tensions between Turkish and English supporters in previous years but the England camp was also wracked by in-fighting as the Football Association had been forced to avert threats of a player strike after Rio Ferdinand had been excluded from the squad over his failure to attend a drugs test with Manchester United.
Against that backdrop, England did superbly to shut Turkey out and secure a 0-0 draw which saw them qualify for Euro 2004, but the match was not without incident. Turkey keeper Rustu Recber almost decapitated Kieron Dyer with a flying challenge; Beckham was guilty of skying a penalty high into the air; and the England captain was also involved in a physical confrontation with defender Alpay that spilled over into a full-blown tunnel bust-up. As Rustu said: "We did no talking about tactics at half-time and about how we were going to beat the English. All we were doing was fighting and, once we got to the dressing room, talking about the fight."
What happened next? With an 18-year-old Wayne Rooney banging in four goals in the finals in Portugal, anything briefly seemed possible for Eriksson's England. But then the Scouser broke his metatarsal in the first half of the quarter-final against the hosts and England were doomed to yet another penalty disappointment. Ferdinand missed the finals due to an eight-month suspension.
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World Cup 2010: England exact revenge
As we saw in yesterday's look at England's darkest days in qualifying, a defeat to Croatia in 2007, ending their hopes of reaching Euro 2008, was one of the most traumatic nights in the country's sporting history. What occurred at Wembley two years later, then, was cathartic on a national scale.
Drawn to face Croatia again, England, this time under the rather more steady hand of Fabio Capello, had already enjoyed a 4-1 win in Zagreb which game them control of the qualifying group, and now needed a win to guarantee their place at the World Cup in South Africa. As it transpired, Slaven Bilic's side were on the end of another thumping as England won 5-1, Frank Lampard and Steven Gerrard scoring twice and Wayne Rooney claiming the fifth. "We didn't expect such a crushing defeat," said Bilic. "Not in our worst nightmares were we expecting this. It was not a normal defeat. It was humiliation."
What happened next? England performed pretty woefully in the finals. An opening draw to USA was followed by unconvincing results against Algeria and Slovenia before Germany absolutely tore Capello's England to shreds in the second round. The Italian clung onto his job, only relinquishing it in 2012 following the John Terry controversy.