For those tasked with curating the new Tottenham Hotspur museum, the club's 1999 League Cup win presents a conundrum; how to display a victory so closely associated with a wildly unpopular chairman (Alan Sugar), a loathed manager (George Graham) and a reviled captain (Sol Campbell)?
But this is revisionist history. At the time, beating Leicester City at Wembley felt hugely significant. And, truth be told, given Tottenham's paucity in the silverware stakes over the past three decades - one further League Cup win in 2008 - Spurs can ill afford to expunge 1999 from memory altogether.
It's worth recapping here just how bad the 1990s were at White Hart Lane. At the start of the decade, financially the club was on its knees. Only an FA Cup win and Alan Sugar's investment staved off financial ruin in 1991. Sugar deserves credit for that, but like all 'good' disaster capitalists his intervention came not from a sense of altruism or deeply-held love. Owning Spurs paved the way for Sugar to make money - lots of money. As Tottenham chairman, Alan Sugar secured the casting vote determining whether ITV or Sky won the broadcast rights to the newly formed Premier League. As Sugar's company Amstrad produced satellite dishes, Sky's victory proved incredibly lucrative for him. The subsequent football-boom sparked by the Premier League's success would eventually allow Sugar to cash out his initial £5million investment in Spurs for a cool £47million. While in 2007 an eternally grateful Sky took Amstrad off Sugar's hands for £125million.
This personal success for Sugar did not translate into triumph on the pitch for Spurs. As the 1990s progressed, Tottenham began to drift badly. A series of catastrophic managerial appointments combined with a refusal to pay the admittedly inflated going rate for top players, saw Spurs vacate their seat in English football's big five. Instead, the world-famous Tottenham Hotspur became embroiled in increasingly fraught battles to stay above the Premier League's bottom three.
The 1997/98 season proved the decade's nadir. Following a poor start under the desiccated management of Gerry Francis, in November Alan Sugar appointed the unknown Swiss, Christian Gross. It was a decision that dumbfounded British football. Especially when Gross arrived for his press-unveiling clutching a tube travelcard, which in broken English, he proclaimed as the ticket "to my dreams". As Alan Sugar reflects in his autobiography, "I knew from that moment - Gross was dead meat."
The downward trajectory of results continued. A 6-1 home defeat inflicted by Chelsea ranked among the very darkest days in Spurs history. It took until the season's penultimate weekend for Tottenham to secure their Premier League survival.
After such a near miss, drastic change was required to avoid a repeat performance - or worse - in the 1998/99 campaign. It did not arrive. Gross's only summer signing was the unheralded left-back Paolo Tramezzani, signed for a small fee from Piacenza. The Italian would be jettisoned after just six appearances.
Tottenham started the season with a 3-1 loss away to Wimbledon and were battered 3-0 in their first home match by Sheffield Wednesday. With invective raining down on Sugar from the White Hart Lane stands, the Tottenham chairman's mind was made up. Gross must go.
Sugar's choice of successor did little to encourage rapprochement. To many fans, George Graham was the antithesis of what it meant to be Tottenham. As both player and manager, Graham was a bonafide Arsenal legend. He had forged a richly deserved reputation for dour defensive football, and (whisper this bit quietly) an undeniable knack for winning trophies. Under Graham's stewardship, Arsenal won the title in 1989 and 1991, the League Cup in 1987 and 1993, the FA Cup in 1993 and the 1994 European Cup Winners' Cup.
Before Graham's appointment was confirmed, Tottenham had already edged into the League Cup third round - beating fourth-tier Brentford 6-4 on aggregate. His first match in charge came away at Pride Park. The performance was textbook George Graham. A 1-0 win secured against the run of play via captain Sol Campbell's thumping header from a David Ginola free-kick. A post-match conflagration saw a fight break out between rival players, leaving a Derby steward with a broken arm and Sol Campbell facing an assault charge. Although the case was eventually dropped, Campbell would later claim that Tottenham's failure to support him during the investigation was the genesis of his eventual split from the club. But that was all in the future.
Campbell was on the scoresheet again as Spurs comfortably dispatched Northampton 3-0 in the League Cup's Third Round. Liverpool away in Round Four presented a far sterner assignment. Ahead of the game much was made of Tottenham's appalling record at Anfield (plus ça change) and the recommencement of hostilities between David Ginola and Liverpool's newly appointed co-manager Gerard Houllier. Houllier had branded Ginola "a murderer" for his role in France's failure to qualify for the 1994 World Cup.
With Michael Owen and Robbie Fowler paired in attack and a raucous crowd behind them, Liverpool flew at Tottenham from kick-off - hitting the bar inside the opening minute. Sixty seconds later, Anfield went silent. Sol Campbell's long diagonal ball was met by the leaping Steffen Iversen, who from 18 yards sent a looping header into the top corner of Brad Freidel's net. The lesser-seen John Scales, making perhaps the only positive contribution of his brief Spurs career, doubled the lead with twenty minutes played. Darren Anderton's long free-kick eluded the home defence and - under pressure from Iversen - Friedel spilt the ball to Scales who could not miss. 2-0.
At half-time, Ginola was substituted by Graham. Ginola's early withdrawal in matches - as flair was sacrificed in search of solidity - was a recurring theme of Graham's Tottenham tenure. It would become a running sore for the White Hart Lane faithful. The flamboyant Frenchman was their darling. On this night at Anfield, Graham's judgement proved sound enough. A cool finish early in the second half by Danish midfielder Allan Nielsen put Spurs three ahead. And despite Michael Owen's consolation, Tottenham cruised through to the last eight in some style.
Manchester United were the visitors to White Hart Lane in the quarter-finals. By the end of the season, Alex Ferguson's side would complete a historic treble. Tottenham inspired by the magnificent David Ginola - enjoying his best performance in a Spurs shirt - ensured there was no prospect of a United quadruple. The Old Trafford club, fielding what David Lacey in The Guardian described as a mix of "regulars and occasionals", held Spurs at bay until half-time.
After the interval, however, Ginola was irrepressible. Within three minutes of the restart, the Frenchman's deft pass began a move that concluded with the diminutive Ruel Fox nodding a ball towards Chris Armstrong to head home. Three minutes later, Ginola raced down the left-wing, producing a mesmeric series of step-overs before whipping a teasing cross to the near post. The darting Armstrong arrived right on cue to double Tottenham's lead, flashing his header past Raimond van der Gouw. Typically Ginola ensured his genius received full recognition - racing to the nearest television camera rather than his team-mates to celebrate. There must have been a spate of cut knees across North London as children tumbled on tarmac playgrounds trying to replicate such a sublime piece of skill.
Teddy Sheringham - roundly booed throughout having quit Spurs for United in the summer of 1997 in search of silverware - set up a nervous final twenty minutes when he pulled one back. But it was Ginola's brilliance that sealed Tottenham's place in the semi-finals. Picking up the ball 25 yards from goal, the winger skipped past Ryan Giggs before arrowing an unstoppable, swerving drive into the net.
Tottenham's league form was far less encouraging. Following the victory over United, Graham's Spurs embarked upon a run of just two wins in 11, a sequence that also saw Spurs fail to score in five of those matches. The football the team played between the 16th January and the 16th February was particularly turgid. Not uncoincidentally, Spurs faced Wimbledon no less than five times in that period. It was the sporting equivalent of purgatory. The way Joe Kinnear and George Graham played the game, football could never be the winner. A 0-0 league draw at White Hart Lane came first. Next up was an FA Cup Fourth Round tie at Selhurst Park which, ending 1-1, necessitated a replay. Before that could be played the two sides were scheduled to meet at White Hart Lane in the first leg of the League Cup semi-final. Those fans who managed to stay awake endured another dire 0-0. Six days later on the 2nd February - appropriately enough the day Americans celebrated Groundhog Day - it was back to White Hart Lane for the FA Cup replay. Wimbledon rotated their side, prioritising the upcoming League Cup semi-final second leg. Spurs, thanks to a brace from Allan Nielsen and an Andy Sinton goal, ran out 3-0 winners.
And so to Selhurst Park for a place in the League Cup Final. An attritional first-half played on an awful pitch was devoid of both quality and chances. As half-time approached those in the densely populated away end had already begun discussing which five Spurs players they'd entrust in a penalty shoot-out. But before these lists could be finalised, Steffen Iversen scored a sublime goal out of nothing. Kenny Cunningham, failing to make a routine clearance, presented the striker the chance to send a lobbed half-volley over Neil Sullivan and into the top corner from the edge of the box. With Sol Campbell in imperious form Spurs held on. The final whistle sparked a mass pitch invasion from the delirious Tottenham fans. Doubtless reflecting in equal measure both excitement at the prospect of a trip to Wembley and relief at not having to play Wimbledon again for at least six months.
For a generation of Spurs fans, it was their first opportunity to see Tottenham Hotspur play at the twin towers. Entering the tired old stadium - by this stage, one of the very worst places to watch football in the country - they could be forgiven for wondering what all the fuss was about. With Martin O'Neill's conservative Leicester City the opposition, it promised to be another cagey affair. With a profound sense of irony, Robbie Williams' Let Me Entertain You blared out as a pyrotechnic display greeted the teams onto the pitch. A stiff wind blew the residual smoke into the players' faces. Many could be seen coughing uncontrollably and shielding their eyes as they walked to the half-way line for the playing of the national anthem.
Over the winter Graham had bolstered his squad with three signings; Mauricio Taricco an Argentine left-back who had impressed during his time at Ipswich; Steffen Freund a ball-winning, one-time Germany international from Borussia Dortmund; and Tim Sherwood, the box-to-box midfielder and captain of Blackburn's 1995 Premier League winning side. Of the trio, only Freund was not cup-tied for the Wembley showpiece. Had Taricco and Sherwood been eligible for selection, Justin Edinburgh and Allan Nielsen - the men who came to define this final - would not have played.
Leicester, who had lifted the League Cup as recently as 1997, came intent on stopping Ginola. Robert Ullathorne was tasked with shadowing the winger’s every move, thus neutralising Tottenham's biggest threat. If Ginola were somehow able to escape Ullathorne’s attentions, a combination of Izzet, Lennon or the pugnacious Savage immediately descended upon him. Chances were unsurprisingly at a premium. Leicester's best came following a rare error from Campbell who failed to intercept a through ball aimed for Heskey. As the young striker advanced on goal, the much-maligned Ramon Vega came to his captain's rescue with a lunging block.
Tottenham's only real chance fell to Iversen. The Norweigian rose well above Leicester's three centre-half behemoths to meet Anderton's cross but saw his headed effort saved by Kasey Keller.
David Lacey's match report for The Guardian described the contest in less than glowing terms. "For a pub match, the football would not have been without merit. But for a major final at Wembley, it was a profound disappointment." Lacey was being generous.
Finally, with an hour played, the game sparked to life. Justin Edinburgh's loose touch on the half-way line invited a forceful tackle from Robbie Savage. As the pair rose to their feet, Edinburgh petulantly slapped Savage on the back of the head - or more accurately on his flowing hair. Having at first turned towards Edinburgh to have a go back, the Leicester man - seeing the referee in his vicinity - suddenly clutched his face, bent double with pain. It was an unedifying spectacle worthy of World Wrestling Entertainment. But, by the book, Edinburgh had to go.
The numerical advantage did little for Leicester. They were a side lacking imagination, crafted primarily to spoil. Tottenham dug in. Anderton ran himself to a standstill. While the wily Freund set about trying to induce Savage to commit a foul worthy of a second yellow card. The Welshman had been booked for his part in the Edinburgh incident. On several occasions, he came close to seeing red.
As the fourth official prepared to confirm how much injury time would be played, disaster almost struck Spurs. Ian Walker came out of his area to usher to safety a ball sent down the channel by Savage. Under no pressure, the goalkeeper slipped, gifting Tony Cottee with an unguarded net to aim at. Rather than shooting from an acute angle, the striker played the ball across the box which fortunately for Spurs fell to Stephen Carr to clear.
Before the heart rates of those in the stands could normalise, Tottenham launched one final attack in injury time. Anderton found Les Ferdinand dropping deep. The striker spun the ball out to the right-wing where Steffen Iversen was galloping. Tearing past the lumbering Steve Walsh, Iversen mustered the energy to drive into the box. Pleasing football coaches up and down the country, the forward angled his shot across Kasey Keller who could only parry the ball into the six-yard box. There, swooping to conquer the League Cup with a diving header, was Allan Nielsen. 1-0 to the Tottenham.
Unwilling to sing George Graham's name, Spurs fans belted out their new anthem as Sol Campbell led the team up Wembley's famous 39 steps. "Man in a raincoat's blue and white army."
For a brief moment, it seemed possible that Tottenham were on the cusp of sustained success. Such optimism proved fleeting. Tellingly in his 589-page autobiography, Alan Sugar dedicates a total of one sentence to the only tangible on-pitch success of his reign. Even that is in the context of sniping at George Graham. Graham, says Sugar, waited less than 24 hours after the final before asking for his cup-winning bonus.
The Wembley win guaranteed Tottenham their first European football since 1991/92. But rather than building upon the two legitimately world-class players in their squad - Sol Campbell and the 1999 Football Writers’ Player of the Year David Ginola - Spurs squandered the moment. That Summer Graham signed Wimbledon's Chris Perry and former Dons midfielder Oyvind Leonhardsen. In the new season, Tottenham tanked. The League Cup was surrendered in a humiliating Fourth Round defeat at second-tier Fulham. The European adventure lasted all of two rounds - a perfunctory win over Moldovan side Zimbru Chisinau before a dispiriting loss to Kaiserslautern. In the FA Cup Spurs were humbled 6-1 in the Third Round. While in the league, Tottenham toiled to a 10th place finish. Graham’s severely strained relationship with the Tottenham crowd plumbed new depths in the close season after he sold Ginola to Aston Villa.
As Spurs started the 2000/01 campaign slowly, the recriminations began in earnest. Graham pointed to a lack of funds for players. Sugar blamed his manager for wasting money. Neither would be at Tottenham for much longer. In February 2001 ENIC relieved Sugar of his controlling stake in the club and - in short order - Graham was sacked by new chairman Daniel Levy for an opaque breach of contract. A run of one win in seven league games before the axe fell - including a spell of four successive nil-nil draws - did little to help Graham's cause.
Of much more significance than Sugar or Graham's departure, Sol Campbell failed to accept Tottenham's offer of a new contract. With the team finishing the 2000/01 season in lowly 12th position few could blame him. For all but the most benevolent of Spurs fans, however, Campbell’s decision to sign for Arsenal under the Bosman ruling proved unforgivable.
Suffice to say back at the Tottenham Hotspur museum - when it opens - the audio guide has some explaining to do.