Most Heartbreaking Moment in Every Premier League Team's History

From relegation to financial woe, from injury to mismanagement, every club knows what it means to feel rock bottom and to encounter the loneliness of despair.

For many of these teams, the reality of hardship has been made all the more impossible to bear due to the vague memories and whispers of success, and past glories that haunt fallen giants and besieged champions.

While this list represents a potpourri of catastrophe, all of which have greatly affected those involved, there is a major line to be drawn between those life-changing events that have overlapped with football, the tragedies and the disasters, and the failings that unfold on the field of play.

All of us have endured the loss of three points or the slipping away of a much-coveted title, but there is little parallel to be made between that ache and some of the other calamities that have touched the English game. 

Arsenal: The 'Final' Hurdle

From the mesmerising successes of the early Noughties, through to "the Invincibles" season of 2003-04, Arsenal established themselves once again as one of the country’s finest clubs. Despite never being able to regain the title, Arsenal finished inside the top two in eight of Arsene Wenger’s first 11 seasons as manager.

Few could have expected, when they won the FA Cup in 2005, that eight years later they would still be without a trophy. Surely no one could have foreseen that a club boasting the likes of Cesc Fabregas, Patrick Vieira, Dennis Bergkamp and Robin van Persie would go on to become such a joke over the following years.

Arsenal’s recent history has been defined by a lack of success, a reality that has become apparent in two demoralising finals.

While the Champions League loss to Barcelona in 2006 was heartbreaking—not least because of the fact that Arsenal led with a quarter of an hour on the clock, I could argue that the Carling Cup defeat in 2011 was even more galling.

By then, the absence of a trophy was becoming critical, and a Wembley final against Birmingham City should have been the perfect occasion to put the demons to rest. Despite dominating the contest, however, Arsenal were unable to find a winner, and Wenger watched on in horror as a mix-up between Wojciech Szczesny and Laurent Koscielny on 89 minutes allowed Oba Martins to ghost in and score—seizing victory for the Blues.

The trophy drought continues…

Aston Villa: European Histories and the Failings of Youth

Not everyone knows about Aston Villa’s history. Not everyone knows, in fact, that the club once stood at the pinnacle of Europe. Then only the fourth English club to do so, they won the European Cup in 1982, beating Bayern Munich 1-0 in the Rotterdam final.

From the top of the mountain, Villa fell very swiftly and were relegated in 1987. Even though they were only out of the top flight for one season, the post-European Cup decline has meant that Villa have been unable to capitalise on their triumph and don’t have the status nor the reputation that is associated with other past winners.

Back in 1987, as now, the Villa team was crammed with youngsters, many of whom had great promise. With the club failing to beat the drop, however, the side disbanded, and players such as Steve Hodge, Martin Keown, Tony Dorigo and Paul Elliott, who could have gone on to have become Villa legends, became so elsewhere.

Having won only two of their final 23 games, the Villains were long destined for the second tier; the malaise of 1987 a stark contrast to the magical success of ‘82.

With the side still in contention for relegation this time around, fans will be praying that another young squad doesn’t fall victim to the dreaded drop.

Chelsea: The Wizard of Os and an Exile Too Far

While the Chelsea of today has a rouble-laden identity all of its own, the club previously had another projected image, one which gave it a soul and a character that traveled across the country.

Following their league triumph in 1955, the club endured a handful of tough years before blossoming back into life for the second half of the '60s. During these years the club were regulars in the top half of Division 1, and under Dave Sexton, enjoyed a magnificent existence, making six domestic and continental cup finals between ’65 and ’72.

The King of the Bridge at this time was Peter Osgood, a striker and Berkshire boy who bled blue and adored the club he felt privileged to play for.

Ossie may have been let down by his off-field approach to life, but while current Chelsea hero John Terry has often been pilloried for his nastiness and cynicism, Osgood’s misdemeanours were apparently much more light-hearted.

However, for the local star, genuinely in touch with the fans, Osgood’s time at Chelsea was occasionally tinged with sadness. Ebullient and overzealous in trying to recover from a horrible broken leg, he endangered his further fitness through negligence toward his own recovery.

Eventually, his lifestyle and outspoken nature drew a wedge between player and manager, and Sexton sent him away from his beloved Stamford Bridge, selling him to Southampton in 1974. Former Daily Mirror deputy chief football reporter Nigel Clarke recorded that departing West London broke Ossie, and he was never the same player again. (Nigel Clarke, 'The Wizard of Os', in Forgive Us Our Press Passes, ed. Christopher Davies)

His final years were beset by arthritis in both knees, and the Wizard of Os died prematurely in 2006 following a heart attack.

The Blues had lost a true great, one whose character had both made him and broken him.

Everton: Heysel Hangover

It is one of the great ironies in football that whilst Everton enjoyed one of the most successful periods in their history, they were denied the chance to cement their reputation on the European stage by their city rivals Liverpool.

The Heysel Stadium disaster of 1985 saw 39 Juventus fans lose their lives just before the club’s European Cup final with Liverpool. The Merseyside club’s supposed culpability in the tragedy saw UEFA move to ban English clubs from European competition indefinitely.

A total of 20 clubs were directly affected by the ban during the years it was imposed, and while English football was hit hard by the resulting talent drain, few felt it harder than Everton.

The club won the league title in 1985 and 1987, came in second in ’86 and had picked up the Cup Winners’ Cup in ‘85. A sparkling generation containing the likes of Andy Gray, Kevin Sheedy and Neville Southall was denied the chance to perform in the European Cup.

They would surely have been among the favourites, and participation would doubtless have had a major impact on Everton’s global reputation. Instead, the team broke apart, as players sought to test themselves on the continental stage.

While no one could ever truly know the full extent of the damage to the club, it is certain that absence from the European Cup during this golden period changed the course of the club’s history and prevented a great team from truly realising their continental potential.

Fulham: 2 Finals, 2 Failures

Fulham, like many others on this list, have endured sorry encounters with financial ruin and basement-division scraps. The ’95-96 season ended with them finishing 17th in the nation’s fourth tier; a sorry situation for the West Londoners, who had previously spent a decade enjoying top-division life.

I would suggest that the club’s major ongoing search for an honour represents their most heartbreaking moment. Twice, the club have, against the odds, managed to make it to a major final, but on both occasions the players have fallen short when history was in their grasp.

Roy Hodgson famously masterminded the Cottagers’ run to the Europa League final in 2010 before Atletico Madrid proved to be too strong an opponent.

Thirty-five years previously, the club—then in the second division—made it to the FA Cup final. That day, a team containing Alan Mullery and West Ham legend Bobby Moore contested a cross-city final with West Ham.

Tragically for Fulham fans, their heroes fell short, losing 2-0 following an Alan Taylor brace. It was the last time Moore would ever grace the Wembley turf, and the last time—to date—that Fulham made the final.

Liverpool: You'll Never Walk Alone

No incident has left a greater scar on the British game than the Hillsborough disaster of 1989. A total of 96 people died after overcrowding and crushing in the Leppings Lane Stand during an FA Cup semifinal between Nottingham Forest and Liverpool.

The tragedy, the subsequent controversy, the quest and the truth have changed the course of the English game, and transformed the global identity and worldwide image of a club and a city.

While all of the clubs on this list have had their share of heartbreak, none have endured that of Liverpool, when 96 fans travelled up the M62 to watch their team and never came back.

Manchester City: Villa Prompts Meltdown

Like others on this list, Manchester City’s current success is all the sweeter considering the hardships the club has endured in the past. They, like Southampton, Norwich and Fulham, have endured a deep and dark decline, and understand the realities of life for a "big club" in the lower leagues.

Manchester City’s decline began with the 1981 FA Cup final. The first contest saw them in a draw with Spurs before Ricky Villa secured the cup for Tottenham with a delicious winner in the 3-2 replay triumph.

The beauty of Villa’s winner was matched only by the despair of City fans, as this failure triggered a sharp decline; twice in the '80s they were relegated, before a brief stint in the third tier proved to be the nadir at the end of the next decade.

They wouldn't return to the FA Cup final for another 30 years.

Although…saying all of that, Ben Watson’s winner for Wigan in last weekend’s final must really have been felt hard in some quarters of the city! 

Manchester United: Munich

Like Hillsborough, the Munich air disaster is a tragedy that not only devastated a club but also affected an entire nation. Much like the Superga air disaster nine years previous, the Munich crash tore apart a successful team and—in the blink of an eye—reduced a club to despair.

The episode unfolded in the cruellest way for all associated with the club, as Duncan Edwards, the team’s shining light, initially looked like he would pull through before succumbing to his injuries two weeks after the accident—he was only 21.

It is remarkable that Sir Matt Busby led the club to their maiden European Cup only a decade after the tragedy, and these events—both triumph and disaster—became crucial components in the building of Manchester United Football Club.

The club’s most heartbreaking event became the ultimate badge of its unity, togetherness and reverence of history.

It shall never be forgotten.

Newcastle United: Dignity in Dismissal

Few men have rescued a club quite like Sir Bobby Robson "rescued" Newcastle United. The legendary manager, one of football’s true gentleman, was called back to his spiritual home—the North East—at the end of his career, charged with changing the fortunes of the club he loved, following their post-Kevin Keegan decline.

The beloved Robson did a sterling job, guiding the Magpies from the bottom of the Premier League to the top four and firmly into the hunt for European positions. Beyond merely improving the team’s on-field fortunes, Robson crucially brought some much-needed dignity and belief back to a club where they had been severely lacking.

After a handful of successful seasons, Robson was shown the door by Freddie Shepherd—eventually the club decided they no longer required their iconic manager. The club’s decline between 2004 and their recent promotion under Chris Hughton was marked, and included their first relegation since 1989.

Following his departure, Robson faced a new battle—as cancer began to ravage his body.

The coach dealt with this final fight as he had every adversary that he had previously encountered, with dignity and grace, eventually succumbing in July 2009.

Only a month or two before his passing, Robson visited St James’ Park one final time. I had the privilege of being in attendance that day, as the great man—clearly suffering enormously—was presented, wheelchair-bound by now, to the crowd one final time.

The emotion on show was overwhelming, with many acutely aware that such visits would be no more. Newcastle won that day but were relegated shortly afterward.

How they could have done with Robson’s resourcefulness, his courage and his generosity in the years between his premature dismissal and that emotional final appearance; how heartbreaking that Sir Bobby’s final vision of his once-noble club was in the fateful throes of relegation.

Norwich: Knocked for 6

Trawling through Norwich City’s history, and interviewing fans of the club and those associated with the Canaries, it’s clear that the Norfolk-based club have endured their fair share of heartbreaking moments.

Consider, for example, their liquidation in 1917 or the relegation of 1985—serving to mar their League Cup victory earlier in the year.

Instead, I chose to focus on two routs, both of which changed the course of the club’s history. One sending them spiraling into oblivion, the other, even more devastating, but which heralded the turning of the tide.

After nine years in the second tier, the club returned to the Premier League for the 2004-05 season. Despite struggling for most of the campaign, the Canaries gave themselves a fighting chance of avoiding relegation following some inspired Dean Ashton performances.

Victory away at Fulham (who had nothing to play for) would have seen them safe on the final day, but despite the immense traveling support and the early attacking endeavour, Norwich were destroyed—6-0—a result which crushed the optimism around the club and sent them hurtling down from whence they came.

Then, like so many others before and since, Norwich became another giant treading water in the Championship. A ninth-place finish in 2006 heaped the pressure on Nigel Worthington, and soon the squad had been dismantled.

Malaise and instability followed, and it wasn’t long before the Canaries dropped into the third tier under club legend Bryan Gunn.

Life in League One began horribly, and English football sat up and took note when the club were thrashed 7-1 at home by Colchester in their first game in the third tier since 1960. It was a desperate moment for the club—suffering their heaviest home defeat ever—and for club legend Gunn, who endured the ignominy of two supporters ripping up their season tickets in his face during the game, before being sacked six days later.

Fortunately, there is a happy ending for Norwich fans, who enlisted Paul Lambert and moved onward (and upward) from this heartbreaking episode.

QPR: Mourning in Malaise

While the West Londoners’ current plight doesn’t make for very encouraging reading, I don’t believe that it represents the toughest period in the club’s history.

It must be remembered that QPR’s recent return to the top flight emerged from an environment of boardroom and financial controversy.

After a relatively stable berth in the nascent Premier League during the early '90s, the club dropped into the second tier before enduring further relegation in 2001—falling into England’s third league along with Huddersfield Town and Tranmere Rovers.

The unhappiness surrounding the club was compounded over the next few seasons as, despite making an eventual return to the Championship, the Rangers endured multiple managerial changes and boardroom scandals, entered administration and lost two promising young players—Ray Jones and Kiyan Prince—due to the pair’s unrelated deaths.

The malaise of 2001 spread unhappiness in the club for over half a decade, and while not "heartbreaking" per se, it certainly puts the club’s current situation into perspective.

Reading: Routs to Remember

The Premier League has a reputation for being one of the world’s most exciting sports competitions, but Reading know better than most just how thrilling it can be.

Unfortunately, despite playing their part in the EPL’s two highest-scoring games, the Royals have lost both of them!

In 2007 they were hammered 7-4 by Portsmouth at Fratton Park; the defeat was made all the worst by the fact that the Biscuitmen had actually held their own in the early stages, fighting back to level the scores at 2-2 before missing a penalty which would have levelled the score following another Portsmouth goal.

Eventually, the floodgates opened.

Exactly two months later, the scoreline was all but replicated as Spurs took them apart with a 6-4 victory. Dimitar Berbatov scored four on the day, but the demolition was made all the more bitter for Reading as they had taken the lead three times.

The games proved a portent for the issues that would plague Reading all season. Failing to sort out their defensive issues and suffering fiercely from second season syndrome, they were relegated after finishing in 18th position.

Southampton: A Change of Homes and a Change of Divisions

Southampton’s move from the Dell to St Mary’s in 2001 was meant to herald a new era for the Saints. Having achieved a stable existence in the Premier League, the club hoped that a move from their cosy home would take them to the next level.

Well…it certainly took them to a new level, but I doubt it was the one Soton were hoping for. The 2004-05 season saw the club dogged by instability, and shorn of the comforting refuge of their previous home, they crashed out of the EPL—Harry Redknapp overseeing a 20th-place finish.

After 27 years in the top tier, the Saints bade farewell to the Prem.

Few could have expected the turmoil of the subsequent years, but things were to get a lot worse before they got better.

The academy was forced to sell starlets such as Gareth Bale, Theo Walcott and Alex Oxlade-Chamberlain in order to cover their losses, but in 2009 things reached a nadir—the club were relegated to League One, fell into administration and received a 10-point deduction.

It was a desperate plight for a club who, only eight years before, had seemingly taken a major step in the right direction. Only now are the club finally reaping the rewards of their investment—it’s been a heartbreaking slog, but finally the dark days are over on the South Coast.

Stoke City: Matthews and Co. Witness Disaster

Until the Ibrox Stadium disaster in 1971, the Burnden Park stadium disaster was the greatest tragedy in British footballing history.

Stoke City played their part in this dark day for the sport, as they travelled to Bolton for an FA Cup quarterfinal against the Wanderers.

That day, a Stoke team featuring the likes of Sir Stanley Matthews and legendary skipper Neil Franklin were firsthand witnesses as overcrowding in the terraces led to a crush.

Much to Matthews’ chagrin and subsequent regret, the match was allowed to continue, despite the accumulation of bodies lying on the touchline.

In total, 33 people died on that fateful day in March 1946.

Sunderland: Mick's 15

I can only imagine how tough it must have been for noble Sunderland to drop into the third tier for the first (and thus far only) time in 1987. The disappointment was compounded by the fact that Lawrie McMenemy had arrived only two years previously as the highest-paid manager in English football and his reign—which promised so much—was such a bitter disappointment.

However, having witnessed the club’s desperate Premier League campaign of the 2005-06 season, I am going to plump for that as Sunderland’s most heartbreaking moment.

As I alluded to before, SAFC are a noble, historic and dignified club, and to see them and the honest Mick McCarthy fall so short was demoralising.

The club’s return of 15 points was, at the time, an all-time low—fortunately for the club it was surpassed by Derby County’s horrific 11-point season two years later.

Swansea: That Sinking Feeling

A common theme in this piece is the way that near-misses at the top end of competition can lead to disaster and devastation further down the line.

When Swansea City endured relegation from the top division in 1983, fans will have been acutely aware of the club’s previous form. In 1965 the Jacks lost their place in the second tier, and had to wait 15 years before regaining their spot in that level.

Despite this, few could have imagined the depths the club plunged to following their 21st place finish in Division One in 1982-83.

The season after they were once again in 21st place, but this time they dropped into the third tier; the decline continued, and less than two decades later, the club were a result away from a further relegation—this time to non-league—escaping at the expense of Exeter City.

The two decades of wilderness were also characterised by financial meltdown and animosity between board and fanbase—it is remarkable just how far Swansea have come since the dark decades scrabbling around in the lower echelons of the football league.

No wonder that after such an exile from glory, Swans fans are living and breathing every inch of their current Premier League and League Cup successes. 

Tottenham Hotspur: A Tale of Heartbreak

Spurs and heartbreak have become familiar bedfellows over the years. Having endured the aches and the misery firsthand, I found it very hard to narrow down the club’s relative tragedies to just one immortal moment.

The late-season disappointments have become worryingly routine, but they still carry with them a pang of emotional loss. The lasagne fiasco of 2006, the Chelsea Champions League triumph last year and perhaps, even this season, a similar fate awaits.

The loss of John White, in 1964, was before my time, but was another event that affected the club deeply. Scotsman White had been an influential inside right in the double-winning team of 1961. Nicknamed "The Ghost," he possessed a delightful array of skills, and was, perhaps, the Glenn Hoddle of his day.

White was tragically struck down by lightning at the age of 27 while seeking cover beneath a tree during a thunderstorm.

I was also struck particularly by the legendary declines of Ossie Ardiles and Hoddle himself when they returned for coaching roles at the club. Often, legends can prove to be the ideal figures to galvanise and regenerate a side, but while both impressed sporadically with their creativity and tactics, the pair left with their reputations tarnished.

Despite still being adored by the fans, the ill-fated managerial spells of two of the club’s genuine greats has forced unhappy footnotes into their relationship with Spurs.

Finally, for heartbreak encapsulated in a single moment, I would choose Paul Gascoigne’s horrific injury in the ’91 FA Cup final. Spurs may have won the contest, but Gazza’s ruptured ligaments set him back 15 months, and he struggled to regain his lustre and verve following the setback.

The Albion: Record-Breakers

Albion fans, look away now—any recap of the 1985-86 season makes for uncomfortable reading. After the promise of the 1970s, and Ron Atkinson’s brief, successful reign, optimism was high around the Hawthorns.

Unfortunately, the promise couldn’t last, and several years of gentle decline led to the horror show of ’85-86.

The Albion were certainly record-breakers this season, but unfortunately they were an unenviable clutch of records—they won a mere four games all season, recorded a remarkable 26 defeats and picked up the lowest points total over a 42-game season.

The Throstles didn’t budge from the bottom of the table following Game 3, and an unlikely trio of managers came, attempted and failed to achieve stability. Relegation preceded a spell of 16 years outside the top fight, including a devastating descent into the third tier.

West Ham United: An Icon Ignored

West Ham United, like several other clubs on this list, have had to endure the loss of a club icon. However, while most clubs revere the men who have put them on the map, only recently have the Hammers begun to treat Bobby Moore’s memory with the respect and reverence it deserves.

While the club were quick to put on a show for the 20th anniversary of the great man’s passing, I agree with Harry Redknapp, that the club’s previous neglect of their greatest-ever player has been little short of “heartbreaking.”

In the years prior to Moore finally losing his tragic battle with cancer, he was often shunned by the club, who seemed incapable of realising the national institution they were lucky enough to possess.

One infamous anecdote recounts England’s greatest-ever captain being ejected from the ground on one occasion when he went to watch his former club—who he served for 16 years. The club secretary had apparently indicated that the nation’s golden boy would have to pay for the privilege of watching his beloved Hammers battle it out in Division Two.

He never again returned to Upton Park—a heartbreaking end to one of English football’s most enduring relationships. 

Wigan Athletic: Impending Heartbreak...?

Having enjoyed a meteoric rise from the foot of the football league to the EPL following the generous donations of Latics chief Dave Whelan, the heartbreaks have been few and far between for Wigan fans in recent seasons.

How ironic, and how cruel, that this season, the site of their greatest triumph may also be the site of their most devastating loss.

While no one in attendance will ever forget Ben Watson’s injury-time winner against Manchester City which earned the club their first major honour, the spectre of relegation looms now larger than ever.

Wigan—and particularly current boss Roberto Martinez—have often worked wonders to steer clear of the relegation places in recent seasons, but this year may prove to be one step too far—at the time of writing the club are deep within the mire and looking unlikely to pull free.

While relegation would surely be devastating for the club and would surely take the gloss off the terrific cup win, fans can be optimistic that the club’s spirit would help ensure they are not too far departed from the top table should they succumb to the drop.