The most heartbreaking moments from English national team history

Liverpool's Goodison Park was the site of what remains one of the most historically significant football moments in the history of the Ireland national team. In a friendly on 21 September 1949, England welcomed their Irish neighbors. This wasn't the strongest English side to take the pitch, but the likes of Billy Wright and Tom Finney were among the Starting XI. England were the offensive aggressor early, but Ireland weathered the storm and broke through on Con Martin's 38-minute penalty strike. They then added on in the later stages through Everton's own Peter Farrell. The result: a 2-0 victory for Ireland, which dealt England their first defeat to another nation at home.

One year after England was stunned by Ireland, the national team suffered an almost unthinkable defeat on the grandest of all stages. Making their World Cup debut in 1950, with Brazil as the host nation, the Three Lions already had a group-stage victory under their collective belt and were favored heavily over their upcoming opponent from the United States. The two sides could not have been more different in both talent and prominence; England were football giants while the U.S. team were rather piecemeal. However, England failed to convert on a number of offensive chances throughout the match, and the match's only goal came in the 32nd minute, when the ball oddly glanced off the head of America's Joe Gaetjens and into the back of the England net, and held up for the 1-0 upset scoreline. English pundits and media types at the time simply called the result "unbelievable." 

England were two years removed from their jubilant World Cup triumph when the European Championship rolled around. It was almost second nature to believe a dynasty was in the making. When reaching the semi-finals against Yugoslavia, the English found themselves in a physical fixture, often borderline unacceptable when considering the grace and honour of the game. England's frustration built and perhaps led to Dragan Džajić's goal for Yugoslavia on 86 minutes. That held up for a 1-0 unexpected victory over England, which went on to place third.

On 17 October 1973, England needed to top Poland on the friendly pitch at Wembley to qualify for the West German-hosted 1974 World Cup. Prior to the match, and apparently due to an overabundance of confidence, Three Lions' striker Brian Clough remarked that Polish keeper Jan Tomaszewski was a "circus clown in gloves." Well, said "clown" was the one laughing and celebrating when the final whistle sounded. Though England were credited with 36 shots, 26 corners and hit woodwork more than one time, the match ended in a 1-1 draw. The result kept England out of the World Cup for the first time since their 1950 debut.

Determined to return to the World Cup finals after missing out in '74, England had their collective hands full trying to get back to that competition for the '78 installment. In the end, it would not happen, as the Three Lions' hopes were dashed, notably, amid a 2-1 loss to Scotland at Wembley. Strikes from Gordon McQueen and Kenny Dalglish helped Scotland win the prestigious Home International Championship — settled between the U.K.'s four countries — and led to their fans joyously storming the famed London pitch.

There's heartbreak, then there is plain frustration that comes from a sense of potentially being short-changed. Both were experienced by England in the quarterfinals of the '86 World Cup against superstar Diego Maradona and mighty Argentina. Maradona scored five goals during the tournament, with two of the most famous coming just after halftime in the 2-1 victory over rival England. Maradona's infamous "Hand of God" goal punch was followed by what's called the "Goal of the Century," as he dribbled some 50 yards through the English defense. The first was controversial, while the second was simply another underachieving moment for England.

Four years after the sting of Maradona, England were back in the World Cup and managed to post their best finish since the '66 celebration. A side mixed with old standbys and new blood, England made a rather surprising surge to the 1990 semi-finals versus West Germany. Down 1-0 after Andrea Brehme’s deflected goal on the hour, England leveled through Gary Lineker in the 80th minute. The match went to penalties, where it can be argued the Three Lions' curse in that area on the international stage was truly born. The West Germans won that format 4-3, and England was relegated to the third-place match, which they also lost, 2-1 versus Italy.

Considered one of the biggest failures in the history of English national football was the nation's inability to qualify for the 1994 World Cup. With Graham Taylor at the helm, England didn't seem to have too tough a qualifying draw for group play. However, the Three Lions managed just one point in two matches versus upstart Norway, highlighted by a 2-0 loss at Oslo in June 1993. Then in October of the same year, a frustrating 3-1 defeat to the Netherlands essentially ended England's hopes of a World Cup position. The whole experience remains a dark cloud over England football to this day.

Following a poor showing in Euro 1992 and not qualifying for the '94 World Cup, one could argue the mid-1990s were the lowest moment in the history of the England national squad. However, the Lions' run to the semi-finals of the '96 European Championship on home soil breathed new life into the hopes of England fans. Of course, that hope would be dashed through a completely disheartening loss to Germany in the semi-finals. The match sat 1-1 after 90 minutes. In extra-time, Alan Shearer narrowly missed connecting with Paul Gascoigne on a potential golden goal and Darren Anderton hit the post. The most-deflating moment came via current England manager Gareth Southgate in penalties. Each side converted their first five attempts, then Southgate stepped up, struck and was stopped. Germany's Andreas Möller followed with the winner, sinking hearts all throughout England.

David Beckham is one of the most recognizable footballers in all of the world, and a national treasure in England — at least to most. However, when he was sent off for a rough challenge on Argentina's Diego Simeone in the second half of a 2-2 match in the round of 16 in France World Cup of '98, he became a momentary pariah to his own supporters. Without Beckham, the match went to penalties, where, to no surprise, England lost. The aftermath left England's hero blamed and chastised for the setback. According to Becks himself, the moment is till quite haunting.

When England fall, they tend to go down in dramatic fashion, like in the final match of the group stage from the 2000 European Championship. After losing 3-2 versus Portugal and beating Germany 1-0, England needed a lone point against Romania to reach the knockout round. However, the Lions found themselves in a fight for Euro survival. Michael Owen gave England a 2-1 half-time lead, but Romania equalised shortly after play returned. Then as if the football gods knew it was time to thwart the hopes of England fans, Phil Neville clumsily tackled Viorel Moldovan in the box, which led to Ionel Ganea's go-ahead penalty in the 89th minute to end the Lions' tournament.

David Beckham, and most of England, moved on from the disappointment of the '98 World Cup. Eight years later, it was the superstar's successful free kick on the hour that got the Lions past Ecuador in the round of 16 of the 2006 World Cup. However, when it came time to face Portugal in the quarter-finals, England's offensive woes continued. The match was scoreless with only penalties to decide. So, with history again rearing its ugly head, England succumbed at this point in the competition. They missed three of their four chances from the spot with stars Frank Lampard, Steven Gerrard and Jamie Carragher all failing to convert.

England needed only a draw to secure a spot in Euro 2008 — and likely save Steve McClaren's managerial gig with the national side in the process. Standing in the way was Croatia, who led by two goals at half-time. England managed to the level the match, only for Mladen Petric to score from roughly 20 out within the final 15 minutes to ultimately give Croatia the win on that November day in 2007 at Wembley. One day later McClaren was sacked. 

England can only dream about what could have been if Frank Lampard's goal was actually called a goal in the round of 16 in this 2010 World Cup match. England trailed Germany 2-1 in the 38th minute when Lampard sent a screamer from 20-yards out that bounced off the cross bar and down beyond the goal line. However, Germany keeper Manuel Neuer quickly grabbed the ball and play went on through referee Jorge Larrionda, to the shock and dismay of not only England fans, but those viewing the match around the globe. England seemingly was left shattered after the incident, and succumbed to a 4-1 drubbing.

After drawing France, England earned one-goal victories against Sweden and Ukraine to top Group D at the 2012 Euros. Then it was off to the quarter-finals and a date with Italy. Of course, as if the plot was predictable, the contest went to penalties. This time, however, England appeared to be in good shape when Steven Gerrard and Wayne Rooney converted out of the jump, while the Italians missed one of the first two. But, as always seemed the case, the bottom fell out for the Three Lions as Ashley Young and Ashley Cole both failed, while Italy made good on three straight to win 4-2.

Losing in heartbreaking fashion in the knockout round of a major tournament is gut-wrenching, but failing to make it out of the group stage at an event such as the World Cup is downright criminal. When it comes to England World Cup misery, 2014 is up there with the worst moments in national team history. The Three Lions never won a match, losing to Italy and Uruguay, then playing Costa Rica to a scoreless draw in a meaningless match. It marked the first time since 1958 that England failed to make it out of initial group play.

From the beginning of the 2016 Euro it seemed like this wasn't going to be England's year. The Three Lions allowed a stoppage-time goal in a 1-1 draw versus Russia, then needed their own late heroics from Daniel Sturridge to beat Wales 2-1 before playing Slovakia to a scoreless draw. Though rather uninspiring, England was able to advance to the knockout round, where the underachievement finally caught up with Roy Hodgson's side versus Iceland. It was a nightmare performance from keeper Joe Hart, who allowed two goals within the first 18 minutes, and upstart Iceland hung on for the 2-1 upset. Hodgson resigned from his managerial role soon after.

With the aforementioned Gareth Southgate in charge, England trekked their way to the semi-finals of the 2018 World Cup. And, there was reason to feel good for Lions fans after finally winning in penalties versus Colombia in the round of 16 and taking a 2-0 result from Sweden in the quarter-finals. Things looked even better when Kieran Trippier scored five minutes into the semi-final match with Croatia. England held that 1-0 edge until the 68th minute, when Ivan Perišić equalised. Then, Mario Mandzukic became England's most recent heartbreaker, scoring the eventual winner in the 109th minute. England then fell to Belgium to settle for fourth.

Out of the shadows of the COVID-19 pandemic, England had themselves up to pose as a serious Euro contender. Could football finally be coming home? It sure seemed that way when England faced Italy in the finals of the 2020 Euro at Wembley, which was delayed one year and played in the summer of 2021. The excitement level was off the charts. Luke Shaw gave England a 1-0 lead two minutes into the match, but it was only a matter of time before the Italians would level; it came on 67 minutes through Leonardo Bonucci. Once again, England's fate would be determine via penalties. England's Jordan Pickford proved brilliant, stopping two shots. But once again, it was not to be, as Marcus Rashford, Jadon Sancho and Bukayo Saka missed three straight spot chances and Italy prevailed 3-2 in penalties. Perhaps most disheartening were the disgusting responses to that trio from some England supporters in the wake of the defeat.

Sure, there was hope for greatness as England entered the 2022 World Cup. And even with a scoreless draw with the United States under their belt from group play, England won Group B by outscoring Iran and Wales 9-2. They then took out upstart Senegal 3-0 in the round of 16, setting up a quarter-final date with France. At that moment, stomachs began to turn. And again, a dramatic missed opportunity was the story of the match. Beloved England star Harry Kane leveled the match via a penalty in the 54th minute, but Olivier Giroud gave France the lead back in the 78th. It was in the 84th minute that Kane again stepped to the spot with a chance to equalise. This time, England's hero pulled it well high over the bar and the 2-1 scoreline stood, thus ushering in another moment of misery for Three Lions football.