That said, spending the early hours of May 7, 2006, throwing up in the bathrooms of the Marriott West India Quay might have left even Edward Monkton’s Zen Dog feeling a little bit frazzled. On the brink of their first qualification for the Champions League (or its predecessor, the European Cup) since winning the double back in 1961, Tottenham Hotspur – a club which prides itself on a glorious history that is but lightly sprinkled with tangible success – succumbed to a bug that succeeded where all else had failed for the previous five months, and a team which had not budged from fourth place in the league table since 3 December would be made to wait another four years for a crack at the big time.

What a rollicking ride it had been, though.

• • • •

LEAVING ASIDE THE QUESTIONABLE PEDIGREE of Charity Shields and of the now long-defunct London Professional Football Charity Fund – a near permanent fixture in the White Hart Lane trophy cabinet between 1908 and 1930 – the 1980s lie second only to the Bill Nicholson years of the 60s as Tottenham Hotspur’s finest ever decade. Keith Burkinshaw delivered a pair of FA Cups as well as the UEFA Cup victory of 1984, while successively Peter Shreeves, David Pleat and Terry Venables all guided the way to third place finishes, on the back of the goalscoring prowess of Mark Falco, Clive Allen and Gary Lineker.

Venables led the team into the 1990s with the cup win that traditionally accompanied a year ending in one, thanks largely to a tubby Tynesider (“Is Gascoigne going to have a crack? He is, you know!”) and a jug-eared chap from Leicester (“And Lineker uses him by not using him”); a sense of propriety, though, demands the caveat that they ended the 1990-91 First Division season in tenth. And while a lot changed over the following ten years – the Premier League was born, Luton Town waned, Bradford City waxed, and the foreigners came – come the season that rung in the new millennium, many things were looking pretty familiar in the top division. Arsenal and Manchester United were up near the top. Derby were down at the bottom. Spurs were tenth.

If not quite a lost decade, thanks to a last-gasp diving header from Allan Nielsen in the 1999 League Cup final, it was not far off. Despite a 35-goal season from Gary Lineker, the team finished 15th in 1992; the delirium that surrounded the arrival of Jürgen Klinsmann in the summer of ‘94 carried them no higher than seventh; and so generally uninspiring proved the air around White Hart Lane in those years that in the 1996-97 season – another tenth placed finish, incidentally – their top scorer was Teddy Sheringham with eight.

The new century initially seemed to promise little better. Alan Sugar sold the club in 2001 to the English National Investment Company, which made sharp work of dispatching ex-Arsenal legend George Graham into the tall grasses, but any hard-headedness that may have been brought into the boardroom was yet to translate onto the pitch. New manager Glenn Hoddle underlined the stagnation by producing near-identical league records in 2001-02 and 2002-03, his sides finishing ninth and yet another tenth, before a slide at the start of the following season cost him his job and prompted ENIC to scour the world for a managerial combination that could break Tottenham out of their funk.

Something significant had to change. For a while, it looked like the board had settled on Italian national coach Giovanni Trappatoni, but come the summer of 2004, it was Jacques Santini, a title winner with Lyon before leading France to the European Championships quarter-finals, who took charge. Underlining the upheaval, Santini was to be part of an entirely revamped managerial team which also included two men poached from the Netherlands – the highly-rated Frank Arnesen from PSV as sporting director, and Martin Jol, who had been quietly improving RKC Waalwijk and had reportedly turned down an approach from Sir Alex Ferguson to be his second-in-command at Manchester United, as assistant.

Rarely, even in the cut-throat world of football, can a manager’s tenure have been shorter than the recruitment process which preceded it, but after spending the best part of nine months finding their man, ENIC would lose Santini again after just 13 games. Following the initial exchange of standard-form pleasantries, it soon became clear that the Frenchman’s beef had been with Arnesen, amid strong rumours that Jol, who had been brought into the club first, had been the Dane’s preferred choice as manager. If so, he soon got his wish.

Santini had left his team in ropey shape, with a home defeat to Charlton the day after he had dramatically upped sticks for France the fourth in a run of six straight defeats; but under Jol, confirmed as the new permanent boss just two days later, their fortunes changed rapidly for the better. After a hectic 5-4 loss to Arsenal in his first match – in itself, the first time the team had scored more than twice in a game since February – and defeat to an in-form Aston Villa in his second, a 2-0 win over Middlesbrough was the first of five victories in a row, albeit that the season then slowly petered out into a spluttering ninth place.

Arnesen, however, had been working hard behind the scenes, his efforts bearing fruit in a transfer purple patch that had started with Michael Carrick and took in Michael Dawson, Aaron Lennon, Tom Huddlestone, Jermaine Jenas, Teemu Tainio and Lee Young-Pyo, not to mention serial trophy-winner Edgar Davids. Arnesen’s head was turned by an approach from Chelsea within a year, and he was replaced by Frenchman Damien Comolli, but the pieces were in place.

• • • •

MEANWHILE, ARSENAL WERE FLYING HIGH. A club with more hard-headed history to their name than their north London neighbours, they had nonetheless spent half a century drifting away from their 1930s heyday, and with Liverpool, Newcastle, Aston Villa and a newly-moneyed Blackburn Rovers all sniffing around the league’s higher echelons in the mid-1990s, their two titles around the turn of the decade were at risk of becoming isolated ripples in the landscape. Then, Arsène Wenger happened, and Dennis Bergkamp, and Nicolas Anelka, and Vieira and Petit, and Thierry Henry; and suddenly, the Gunners had hit the sweet spot.

For seven years between 1997 and 2004, the league became a carve-up between them and Manchester United, the climax coming in the extraordinary unbeaten season of 2003-04. An inevitable comedown left them trailing the following year, while an ever-improving Chelsea were beginning to muscle in on the hegemony, but even then it was United, not the Gunners, who were being knocked down to third.

Not that they weren’t a touch worried in N5 come the autumn of 2005. While Wenger’s teams had never missed out on Champions League qualification since being pipped to second on goal difference in 1997, the Frenchman’s hands had been tied for some years by the financial constraints that came with the building of a new stadium a few hundred yards down the road at Ashburton Grove, and the most significant movement in the summer’s transfer window had been outwards, with club captain Patrick Vieira leaving for Juventus.

Meanwhile, Chelsea, now under the management of the new golden boy of European football, José Mourinho, didn’t look like going anywhere, while Liverpool had barely been out of the top five for a decade, and you could never quite trust Newcastle to stay out of mischief.

Spurs – good old unreliable Spurs, with their annual St Totteringham’s Day – were less of a concern.

• • • •

PLUS ÇA CHANGE. Within two games of the new season, Tottenham were top, albeit that both Portsmouth – who had gifted their opponents the lead with an own goal just before half time – and Middlesbrough, who failed to capitalise on a bright second-half performance led by Mark Viduka, could argue the toss about their respective 2-0 defeats.

Plus c’est la même chose. After that promising start, draws with Blackburn, Liverpool and Villa sandwiched a home defeat to Chelsea, while the manager was struggling to find room in his team for both Jermain Defoe and Robbie Keane. All told, though, things could have been worse, and six games in, Jol’s team sat sixth.

Meanwhile, Arsenal had had a couple of wobbles of their own. Defeat at Stamford Bridge was one thing, but two weeks later, Thierry Henry travelled with France to Dublin for a World Cup qualifier, and the aggravation of a niggling injury that he had carried with him meant that he would not see first team action again for a month. The Gunners’ record in the league over that period – two wins, a draw and two defeats – was not in itself a major concern, with plenty of time left in the season to recover, but what was more worrying was the effect which Henry’s absence seemed to have on the team.

Troubled in defeat to Middlesbrough, Wenger accused them of “lacking maturity” in a 2-1 loss to West Bromwich Albion a month later that left them eighth with eight games gone. Henry, the team’s top scorer every year since 99-00, was in danger of becoming less an inspiration than a crutch.

The end of October brought the season’s first north London derby. Honours were shared at White Hart Lane, a late mistake from Paul Robinson allowing Robert Pires to equalise Ledley King’s first-half header, before three wins on the bounce for the Gunners in November, coupled with a slump from early-season high-fliers Wigan, meant that as fans around the country began to peel the foil off the windows of their Advent calendars, order had been restored. Chelsea were top, Manchester United second, Arsenal were third, and Liverpool fourth.

It was the last the Gunners would see of the Champions League places for months.

• • • •

INDEED, HAD SPURS HELD ON to beat their bitter rivals in the last ever north London derby at Highbury, on April 22, 2006, that would just about have been that. With a Tottenham win, the gap between the sides would have been seven points – the largest it would have been all season – and while Arsenal still had a game in hand, courtesy of runs to the latter stages of both the League Cup and the Champions League, Spurs would have needed just one win from their remaining two matches, a home tie with Bolton and a trip to Upton Park, to seal fourth spot.

As they had in the reverse fixture, Tottenham controlled the first half, this time with Carrick and a 19-year-old Lennon to the fore in the Saturday lunchtime sun. Henry and Fàbregas had been surprisingly demoted to the bench for Arsenal, and Spurs looked to be taking full advantage when, shortly after the hour, a collision between Emmanuel Eboué and Gilberto Silva left the Ivorian prone, allowing Davids to play in Keane to score.

At White Hart Lane, Spurs had held on to their lead until 77 minutes into the game; here, there were just six minutes remaining when Emmanuel Adebayor broke down the left, rolling Paul Stalteri, and slipped in Henry, who had stolen a march on Dawson inside the box. It was hardly an easy finish, but in the blink of an eye and with two touches of the Frenchman’s right foot, one with his instep to take it away from Dawson, one with the outside to flick it past Robinson, the substitute had done enough – and quite brilliantly too – to keep his side in the race.

And so, three games to go for Arsenal. Two for Spurs, and their fate still in their hands.

• • • •

THAT IT HAD COME THIS FAR AT ALL was testament to both teams’ generosity of spirit in ensuring that a race that had hardly been anticipated never looked to be over. For if Spurs had kicked for home two or three laps out from the finish, then Arsenal had been poised on their shoulders for all that time, never overtaking, always hovering; and when the Spurs boys stumbled, those behind them stumbled too.

Tottenham had made the first significant move on 3 December, when after another four-game winless run – two more 1-1 draws to add to the one with Arsenal, and a 1-0 setback at Bolton – and an untidy 2-1 win at Wigan’s JJB Stadium sealed by a driving run and finish from Davids, Sunderland came to White Hart Lane. Coming off eight straight away losses of their own, Mick McCarthy’s team fell back early on before Dean Whitehead’s long-range free kick gave them a shock lead. Mido and Keane seemed to have restored order only for Anthony Le Tallec to equalise, and Keane missed a penalty with 20 minutes to go before Carrick finally sealed the win to take his team into fourth.

Arsenal, meanwhile, had suddenly lost their scoring touch, and consecutive defeats to Bolton, Newcastle and Chelsea – the first time, under Wenger, that they had ever lost three league matches in a row – left them down in eighth place a week before Christmas, albeit just five points off Spurs and having played a game fewer.

Games in hand can, of course, cut both ways, and this season, under the pressure of constantly playing catch-up, the Gunners kept on slipping up. A 1-0 defeat to Everton on 21 January meant they failed to take advantage of Spurs drawing with Villa. Tottenham lost at Fulham ten days later; the day after that, Arsenal went down 3-2 at home to West Ham. All told, Spurs won one in six from mid-January, while Arsenal’s defeat to Blackburn on 25 February was their fourth loss over the same stretch, and left both teams on worse runs than Birmingham, who were mired in 18th and would be relegated come the end of the season.

If Spurs’ wobbles were the growing pains of a club unaccustomed to serious contention, it is more difficult to pinpoint what held Arsenal back. A failure to replace Vieira? Perhaps, but the team were well stocked in midfield, with Gilberto Silva a key part of the Invincibles, Cesc Fàbregas an emerging superstar, and Freddie Ljungberg, Robert Pires and summer signing Alexander Hleb all offering incision and thrust. There were no major injury setbacks save for at full back, where Ashley Cole, Gael Clichy and Lauren suffered to varying degrees; and while physioroom.com reports that Arsenal were the fourth most injury-hit club that season in terms of days lost, more than a third of those days are attributable to just two players, Lauren and Abou Diaby.

Whatever the reasoning, come the beginning of March, the Gunners were as close to 12th-placed Everton as they were to Spurs. Happily for Arsenal, however, they had made something of a habit of late-season surges. Four years earlier, they had broken Tottenham’s long-standing record of consecutive wins in a league season, with a string of 13 victories between February and May taking them to the title, while the championship of 1997-98, in Wenger’s first full season in charge, had itself been sealed by ten wins in a row. They were too far back for a title push this year, but on March 4, 2006, they started reeling off the wins again – 4-0 at Fulham, 2-1 against Liverpool, 3-0 against Charlton, 5-0 over Villa. Spurs lost at St James’s Park on April Fool’s Day; Arsenal still had the spare game, and suddenly they were two points behind.

Spurs got in first, and pulled out to five points clear again with a 2-1 win over Manchester City, before Arsenal lost at Old Trafford, briefly allowing Blackburn to poke their noses into the race. Spurs still had to host Manchester United themselves, and duly went down 2-1; Arsenal had beaten West Brom 3-1 two days earlier to bounce back from a draw at Portsmouth, and the gap was back to four points, with that game still in hand, and the derby up next.

• • • •

IF SPURS FELT HENRY’S LATE EQUALISER was the turning point as the season approached its climax, they didn’t immediately show it, and by 30 April, the gap was seven points once more, after an Aaron Lennon goal had given them a 1-0 home win over Bolton. Arsenal – with the added distraction of a Champions League final against Barcelona to come – now faced three games in six days, and they had to win them all and hope.

Two of those matches, what’s more, were away. Arsenal had lacked a cutting edge away from Highbury all season, with just 14 goals scored in their previous 17 matches on the road, and Pires’s White Hart Lane equaliser their solitary strike against any other top-nine team. They were, however, facing the league’s worst defence, that of a Sunderland team which had been bottom since October and had picked up just 12 points in 35 matches, while the other fixture saw them up against Stuart Pearce’s downwardly-mobile Manchester City, themselves coming off a run of seven defeats in eight.

Sure enough, Arsenal eased to a 3-0 win at Sunderland, with all three goals coming in a 14 minute spell before half time. The midweek trip to City proved to be a tougher test, with Freddie Ljungberg’s opener cancelled out by David Sommeil; but eventually the pressure told, and two goals from José Antonio Reyes in the final 12 minutes brought them back to within a point of the prized fourth spot. And so it came down to the last.

And if the story of that final day will forever be mixed up in a questionable lasagne, it is easy to forget that Spurs might not have beaten West Ham anyway. After all, Arsenal hadn’t managed to do so, their only point against the Hammers coming in an early-season 0-0 draw at Upton Park. Alan Pardew had put together an entertaining side that would, the following weekend, come moments away from lifting the FA Cup before an injury-time equaliser from Steven Gerrard, while Tottenham’s win at Wigan in November had been their only away victory all season against a side in the top ten.

In the event, after a frantic and futile attempt on Spurs’ part to get the match delayed, Carl Fletcher gave West Ham the lead before Jermain Defoe’s equaliser gave the Lilywhites hope. Meanwhile, over at Highbury, the Latics were putting up a fight, and found themselves 2-1 up after 33 minutes thanks to goals from Paul Scharner and David Thompson.

It couldn’t last. Sheringham missed a penalty against his former club just after half time, but with ten minutes to go, Yossi Benayoun skipped into the box and smashed home the winner. Back in north London, Wigan, who had long since resigned themselves to mid-table mediocrity in their first ever season in the top flight, had been pushed back, and on a day full of emotion as the Gunners said goodbye to both Highbury and Dennis Bergkamp, Henry’s hat-trick put the final nails in the coffin.

And just like that, it was all over. Jol would lead his team to another fifth place the following year before backroom heads were turned by Sevilla’s Juande Ramos; then, after Ramos had led the team in short order to the jaws of catastrophe, it finally fell to Harry Redknapp, picking off a fading Liverpool and holding off a surging Manchester City, to take Spurs into the Champions League in 2010.

To Redknapp, then, the spoils. But the way had been lit four years before, by an unheralded manager with an unsung team which came from nowhere to the brink of the big time. If now, ten years on, Spurs fans deal in expectation, back then, they were simply daring to dream; and these were the days of their lives.

By Harry Reardon. Follow @hsreardon