A Peek through the Looking Glass: An Alternative Perspective on the Most Dramatic Moment in English Football History

In football, moments of huge significance are often remembered in isolation. The trials and tribulations of the route to that point, the conditions and circumstances surrounding a particular event, or the legacy it ultimately procures are often somewhat overlooked. After all, most of a certain vintage can keenly recount man’s first steps on the moon, but few would go on to narrate the impact of the lunar mission in the context of the Cold War space race.

This concept in the beautiful game has slowly accentuated over time as a society perpetually striving for instant gratification builds around it. The moment, this moment, is everything. 

Jimmy Glass last-minute goal saved Carlisle United from relegation. But it may have also been the inadvertent catalyst behind their future struggles.
Art by Onkar Shirsekar

Most who profess to have a reasonable knowledge of the English game will be familiar with the tale of Jimmy Glass. An on-loan emergency goalkeeper, shipped north from Swindon to the border city of Carlisle in their hour of need, would produce a ‘moment’ inscribed in footballing folklore.

With Carlisle United’s ninety-five-year existence in the Football League hanging by a proverbial thread, the unassuming Glass, having watched his new teammates toil for 93 minutes in a 1-1 stalemate, trotted into the Plymouth Argyle box for an injury-time corner. Nobody could have predicted how the next thirty seconds would unfold. A dangerous, whipped ball was met by a towering header from Scott Dobie, who saw his effort parried by the Argyle ‘keeper. However, up stepped his opposite number, Jimmy Glass, to sweep a low shot in the bottom corner and send Brunton Park into raptures. 

The story has been told, re-told, and then told again, with lovers of the game eager to rejoice in an event that resonates with many. The underdog, down and out, scrapping for survival with their last modicum of hope, turning to an unlikely hero to pull them from the mire; it’s the stuff of legend. Over two decades later, the episode still holds as much precedence in the psyche of those of a Carlisle United persuasion as it did that balmy May afternoon. 

In a region cut-off from the rest of the country, sparsely populated, agricultural, and lacking investment, Carlisle is often a forgotten force in England’s north. With Newcastle sixty miles to the east and Manchester over twice as far to the south, Carlisle is lost in a vast, remote expanse, providing a gateway to the Lake District in the south, and forms the last major settlement before the Scottish border to the north. Indeed, such is the extent of the sprawling land mass surrounding it that Carlisle, unbelievably, is technically the biggest city in the UK, encompassing a colossal area of over 1,000 square kilometres. This makes it nearly four times the size of Birmingham. 

Aside from the catastrophic floods of 2005 and 2015, the Cumbrian capital rarely grabs the headlines, operating harmlessly under the radar as a distant, muted entity. However, for one day at least, Glass’ surreal actions captured the attention and adulation of a nation and threw a spotlight on the city like never before. 

But what happens when Jeff Stelling in the Sky Soccer Saturday studio turns his attention elsewhere? When everyone moves on to the next story? When the dust settles, and everyone returns to business as usual? Many stakeholders in the game, fans, analysts, pundits, and players may have embraced, championed, and relived the dramatic end to the 1998/99 Division Three campaign, but few talk about its consequences. 

An unpopular opinion it may be, but that fell swoop of Glass’ right foot catalysed a significant, sinister change in the club’s psyche. It may well have been the sweetest occurrence in Carlisle United’s rather lightly decorated history, but it was also, ironically, arguably the most damaging. In the five seasons that followed, the Blues failed to register a league ranking higher than 17th, finishing amongst the bottom three sides on four of those five occasions. The event had triggered a new mentality, a belief almost, that the club was destined to battle the odds each year. It was almost as if the miracle was somehow too monumental, unable to happen without some sort of price being paid. At an unconscious level, a seemingly over-powering feeling of indebtedness developed in the hearts and minds of those connected to the club. 

We couldn’t have actually got away with it in this way, could we?

Ultimately, football’s greatest escape pre-empted a protracted slide towards the very conclusion in which it originally had so expertly navigated: relegation from the fourth tier of England’s pyramid system. 

True, the avoidance of demotion on the 8th of May only proved to be a stay of execution. By the summer of 2004, Carlisle had slipped into non-league football after a particularly tumultuous season. However, this was merely the crystallisation of years of poor performance, an inevitable conclusion to a hugely bizarre period. 

To probe into the comings and goings of that era is perhaps for another day; indeed, you could write an entire book about the scandalous Knighton dynasty (which Mr Knighton himself has actually had a go at) which descended upon Brunton Park in the late 1990s. The managerial merry-go-rounds, financial ambiguity, and farcical board leadership seriously served to undermine the product on the pitch. However, these developments merely accelerated the club’s funeral march towards the Nationwide Conference; it was the aforementioned fundamental change in mindset which should go down as the cause of death. 

The following season saw the Cumbrians embroiled in another fight to keep their heads above the league parapet, locking horns with Chester City in their endeavours to beat the drop. Only goal difference preserved United’s Third Division status, finishing two goals ahead of The Seals after picking up just two points from their final six fixtures.

The contrasting energy and dynamism for United’s last day of this season versus the previous time round were stark, succumbing 1-0 to Brighton & Hove Albion, who would begin their protracted ascent to the Premiership a year later. Fortunately, Chester City were unable to take advantage and were themselves subjected to a bruising 1-0 defeat at the hands of Peterborough United. Again, Carlisle had played with fire and yet again emerged unscathed. Well, at least on the surface. 

In the 2000-2001 campaign, the Blues fared little better, finishing 22nd out of a possible 24 and flirting heavily with relegation once more. This time it was north London outfit Barnet who plunged into the fifth-tier, casualties of a four-way tussle for survival. Substitute Carl Heggs had struck home a late volley in United’s penultimate game away at Lincoln City, earning a point that would offer some vital leverage as the league season climaxed. Torquay United and Halifax Town, household names for regular custodians of lower league football, were the other suitors bidding to stay up. In a fortunate twist of fate, the final round of fixtures saw Barnet pitted against Torquay, meaning at least one of Carlisle’s foes were to drop points on the last day—automatically securing the Blues’ place in the division for at least another campaign. 

There was brief respite to come, with United earning what would feel like a lofty 17th place finish in 2002. Unlike the Cumbrians, Halifax Town’s luck had eventually run out, with the Shaymen propping up the final league table in the last position.   

Nevertheless, there were flashes of Déjà vu almost two years later, as the second to last game once again had a telling impact on the immediate destiny of the club. This time United were reliant on hat-trick hero Brian Wake, who netted all three goals in a spirited victory over fellow strugglers Shrewsbury Town. In a game that could only be described as an old-fashioned six-pointer, both sides saw their fate sealed as the Cumbrians ran out 3-2 winners to relegate the Shropshire men. 

In the season’s early exchanges, a wave of optimism had washed through Brunton Park’s terraces. An Irish revolution had descended on the club, with Umbro bigwig John Courtenay putting a halt to Michael Knighton’s disastrous tenure. And, although Courtenay’s inaugural season brought about an impressive LDV Vans Cup run, which saw United just beaten to the competition’s crown by Second Division Bristol City, the Blues couldn’t rid themselves of the now habitual relegation dogfight. Furthermore, a structural change to the league format instantly became a cause for concern. Exeter City crashed out of the division with Shrewsbury Town, as football league executives added a second relegation spot for the first time. It felt as if the net was closing. 

In a cruel irony that only football can serve up, Carlisle United were eventually relegated the following season, subjected to demotion in none other than their centenary year. However, the damage had been done the previous calendar year, with the opening half of the campaign an unmitigated disaster. Cut adrift at the bottom at Christmas, it took a miraculous run of form to get the Cumbrians anywhere close to survival. A disappointing 1-1 draw at home to Cheltenham Town confirmed what many had feared for months, and United were forced to accept their new identity as a non-league football club. 

The worst thing about it? The club had seemingly awoken from its post-Glass slumber. This relegation battle had felt different from the others; the team didn’t sleepwalk through each Saturday afternoon and Tuesday evening for months, only to have their blushes spared by one timely performance or the shortcomings of a rival club. This time, they had attacked the second half of the season with gusto, galvanised by a common goal and a desire to make a step-change. It wasn’t a gloomy procession towards salvation, rather a scruff-of-the-neck style attitude that led to a glorious failure.

Of course, in some ways, relegation brought a sort of twisted relief. A loyal supporter base, weary from the relentless threat of demotion, could now potentially look forward to a season filled with greater promise than just saying clear of danger.

Nevertheless, there had been genuine hope, with good reason, that the club had turned the corner. Free from the psychological shackles inadvertently placed on themselves in the aftermath of Jimmy Glass’ fateful strike, United found themselves in an unfamiliar league. Conversely to recent times, Carlisle now had the right mindset but no longer had an affiliation to the Third Division to go with it. 

While the dream of bouncing instantly back to the Football League was undoubtedly at the forefront of fans’ minds, the looming financial challenge of operating a club on a far more restrictive budget was also a tangible worry. A disturbing pattern had materialised throughout the Cumbrians’ almost annual participation in relegation skirmishes, as those clubs who were beaten to the punch ended up suffering a knockout blow further down the line.

Scarborough Athletic, whose fans had been celebrating on the pitch at the McCain Stadium just seconds before Glass’ historic goal, ended up going out of business less than a decade later. Wound up in June 2007 in relation to debts amounting to over £2.5m, the North Yorkshire side would become the first of an unfortunate list of associated clubs to face liquidation.

A year later, Halifax Town, embroiled in a fierce fight with United in the 2000-01 season, had ceased to exist. At least their phoenix club, FC Halifax Town, now stand on the precipice of a return to the fourth tier. In the spring of 2010, it was the turn of Chester City, who had been put to the sword by the Cumbrians at the turn of the millennium. Chester F.C, the newco formed in the wake of City’s demise, who inherited the old club’s Deva Stadium, now compete in the National League North, two divisions below the Football League. 

However, the dream became a reality as United stormed to a Nationwide Conference play-off final victory over Stevenage, immediately ending their exceptionally short stint in non-league football after a third-place league finish. Moreover, the man who steered the Blues back to the big time was the same individual who guided the club away from its seemingly pathological attraction to relegation scraps.

Paul Simpson, who forged a respectable playing career in the game, having spells at Manchester City, Wolves, and Derby County, assumed the role of player-manager at Brunton Park in the summer of 2003. After the aforementioned catastrophic start to the 03-04 season, which saw United amass just eight points from the opening twenty-one league fixtures, Simpson went on to weave his magic.

Although still rampaging down the left flank and contributing plenty to the side in a playing capacity, it was his ability to summon out the ghosts of Glass-past that catapulted Carlisle into a new era. There was a freedom to their play, a swagger, something which was replicated the following year as United launched their onslaught on the Conference. The hoodoo was now well and truly broken.

After lifting the division’s play-off trophy at the Britannia Stadium following a slender defeat of Stevenage, United reconvened life in the fourth rung of English football, now re-branded as League Two. Astoundingly, the club romped to the title, pipping Northampton to the championship and gaining promotion to League One. Unfortunately, Simpson, who would go on to manage England to Under-20 World Cup glory in South Korea in 2017, was poached by Preston North End just days after his league-winning exploits. Nevertheless, his influence over a relatively short timeframe had altered the discourse, pioneering a new, revitalised approach at United and setting the foundations for a better future. 

It would be overtly facetious to say that the events of 8th May 1999 were the only protagonist towards Carlisle United’s almost uninterrupted five-year duel with its relegation demons. There were many contributing factors towards the most difficult chapter in United’s 118 years of being, from poor recruitment to bad ownership, managerial mistakes to infrastructural inefficiencies. Nevertheless, the chief driver was undoubtedly the hypnotic glaze that consumed the club after Glass’ last day reprieve, utterly in awe of an event that should have been too good to be true.

Coincidentally, Simpson is now back at the helm at Brunton Park. It was no surprise that his appointment coincided with a radical change in form when United, with no wins in eight, won the next four matches on the bounce. Within weeks, under the stewardship of the returning prodigal son, the Blues had steered clear of relegation, retaining their place in a league that Simpson had won in the final act of his first tenure as manager. 

Carlisle may have been a victim of their own miracle, but few Cumbrians would swap that Jimmy Glass goal for anything. 

Perhaps it’s apt to leave you with the wise words of the man himself.

‘It fell to me, wallop, goal, thank you very much.’

Jimmy Glass summarising his history-making finish.

A modest review of a moment whose permutations were far more further-reaching than the folklore tales would come to articulate. 

Carlisle United had peeked through the Looking Glass, and it would take five years to shake off its bewitching effect. 

Ryan Murray

With a lifelong association to football, Ryan Murray has embraced the beautiful game in all guises; as a player, spectator, and now writer. Specializing in the daily soap dramas & cultural nuances that perfectly characterize the chaos of the Scottish game, you can often find him scrolling through endless reams of information about his beloved football club (which will remain unnamed), or alternatively researching a particular bizarre or intriguing (well, at least he finds it so) episode from some distant corner of the footballing world. He resides in Leeds, but appears more often at seventh tier grounds around the urban sprawls of West Yorkshire than at Elland Road - it just feels more like football. He lives with his fiancée and sausage dog, both of whom now support the right club.