On 27 October 2007, Juande Ramos put pen to paper on an eye-watering £6m per season four-year contract to coach Tottenham Hotspur. On 25 October of the following year, that contract would be terminated, Ramos’ time at the helm reduced to a mere interlude between the lengthier reigns of Martin Jol and Harry Redknapp.

But as interludes go, it was certainly a memorable one. Just four months into his spell in charge, Ramos led Spurs to victory in the Carling Cup, the club’s first trophy since winning the same competition in its Worthington-sponsored form nine years previously. Yet, whilst the class of ’99 had secured the cup victory by edging out 1-0 wins over Wimbledon and Leicester, Ramos’ side gave the fans some sweet memories to savour, putting Arsenal to the sword 5-1 in the semi-final and overcoming rivals Chelsea 2-1 at Wembley.

Tottenham’s fans weren’t accustomed to this kind of success, but Ramos was. In his previous stint at Sevilla, he had won back-to-back UEFA Cups in 2006 and 2007, alongside the 2007 Copa del Rey and UEFA Super Cup. Before departing for London, he also had time to squeeze a Spanish Supercopa into Sevilla’s now overflowing trophy cabinet after defeating Real Madrid 6-3 on aggregate in August 2007. Equally as impressive as Ramos’ medal haul was his ability to get Sevilla to compete against LaLiga’s best. In the 2006/07 season, they managed to beat both Real Madrid and Barcelona 2-1 at home on their way to a third-place finish, securing Champions League football for the following campaign.

That kind of success didn’t go unnoticed, and with his contract at Sevilla due to expire at the end of the season, attractive proposals would be forthcoming. One such proposal came from Tottenham chairman Daniel Levy. As the press would soon reveal, Ramos met with vice-chairman Paul Kemsley and club secretary John Alexander at a hotel in Spain. The Spaniard was made an offer that he described at the time as “dizzying” but one which he respectfully turned down.

The newspaper reports of the meeting were embarrassing for Levy, not least because he already had a manager under contract. Dutchman Martin Jol had just secured a second successive fifth-place finish in the Premier League, a marked improvement on the mid-table mediocrity the White Hart Lane faithful had been accustomed to in the Premier League era.

Although popular among the fans, Jol had his doubters in the boardroom, notably sporting director Damien Comolli. The Frenchman had been brought to the club from Saint-Étienne by Levy in September 2005 to replace Frank Arnesen who had been cynically poached by Chelsea. As part of Levy’s continental set-up that he had put in place in 2004, the sporting director would be responsible for player recruitment, and, crucially, manager recruitment as well.

Jol had been brought to the club by Arnesen, and while Comolli had two transfer windows under his belt in terms of player purchases, he was yet to prove to his chairman that he had an eye for spotting talented coaches too.

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By the middle of the 2006/07 campaign, Jol’s side were struggling. As it became clear the likes of Tom Huddlestone and Didier Zokora, who had followed Comolli from Saint-Étienne, were not up to the task of replacing Michael Carrick in midfield, Spurs’ form was worryingly inconsistent. By mid-February they sat in tenth place, ten points off fifth and behind the likes of Bolton, Reading and Portsmouth.

After narrowly missing out on Champions League qualification amid the infamously – though wrongly – named ‘Lasagna-gate’ fiasco (it did, in fact, prove to be a virus and not food poisoning that wiped out most of the first-team squad that day), the Spurs hierarchy was concerned that the club was regressing. The 3-0 defeats against Arsenal and Liverpool and a 4-0 home defeat to Manchester United did nothing to disprove their fears that they were not getting any closer to closing the gap on England’s elite clubs.

The team’s poor form planted a seed in the chairman’s mind that Jol had taken the club as far as he could and a change of coach would be needed. Keen to bring in his own man, Comolli needed no encouragement to help that seed grow and discuss possible appointments, Ramos undoubtedly among them.

A change of fortune was in store for Jol, however, as Robbie Keane and Dimitar Berbatov developed a telepathic understanding that would see Spurs go on an impressive run in the league, losing only one of their final 12 games in the 2006/07 league campaign. At one stage it had looked like Spurs could go on and win a trophy after a 6-4 aggregate win over Braga qualified them for a UEFA Cup quarter-final against none other than the holders, Juande Ramos’ Sevilla. Spurs were unlucky to go down 2-1 in the first leg in Seville after conceding a dubious penalty and fancied their chances of turning the tie around in the second leg under the floodlights of a packed White Hart Lane.

Needing to overcome the deficit, they were expected to take the game to Sevilla with the Spaniards looking to keep it tight and play on the break. Not these Spaniards. Ramos’ players stormed out of the blocks, forcing a Steed Malbranque own goal within two minutes before ex-Spurs man Freddie Kanouté made it two with just eight minutes on the clock. Although Tottenham got two goals back to draw on the night, Sevilla’s two away goals had already put the tie to bed in a fashion fitting of the London club’s motto – ‘to dare is to do’.

Sevilla would go on to win the competition, the images of Ramos lifting the trophy presumably only helping to water that seed of Levy and Comolli’s that was now emerging into a small plant with some leaves of its own.

The side was lacking proven quality players in the middle of the park, and reliable backup for the often-injured Ledley King. Jol could count on the likes of Berbatov, Keane and Defoe to do the business up front, but the spine of the team behind them was in need of strengthening.

The Dutchman must have been left scratching his head that June when the club went out and broke its transfer record that summer, spending £16.5m to bring in striker Darren Bent from relegated Charlton. A 21-year-old defender, Younès Kaboul, was signed from Auxerre and a 20-year-old Kevin-Prince Boateng joined a long list of players who could be considered options in a central midfield devoid of an obvious first-choice partnership.

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In a summer that seemed to be more focused on building a team that would peak in the next decade rather than giving the manager the tools he needed for the job at hand, teenagers Gareth Bale and Danny Rose were signed from Southampton and Leeds respectively.

With defenders King and Michael Dawson both injured, Spurs got off to a dreadful start to the 2007/08 campaign. Ten games into the season the club had recorded just one win, a 4-0 home drubbing of Derby. The decision was taken to relieve Jol of his duties after the UEFA Cup game at home to Getafe on 25 October. But the news was leaked before kick-off as word spread around the ground; Jol himself found out after receiving a text message from his nephew as Tottenham lost 2-1.

There was only one name in the frame when it came to his replacement. Juande Ramos resigned from Sevilla the very next day. Levy had made him a gargantuan offer, but he wouldn’t wait until the end of the season: it was take it or leave it. Whether it was his stated desire to manage in the Premier League or the reported £6m-a-year salary on offer, or perhaps a combination of both, Ramos felt he could not refuse.

The 53-year-old was joined in London by fitness coach Marcos Álvarez and ex-Spurs player Gus Poyet joined from Leeds as Ramos’ assistant. As someone who had played in both Spain and England, Poyet would help Ramos with the cultural as well as linguistic barriers he would face at his new club.

After a mixed start for the trio, the team’s form started to pick up over the Christmas and new year period and they were boosted by the singings of Jonathan Woodgate (the experienced defender Jol was crying out for) and Alan Hutton. Many put this improved form down to the new fitness and training routine put in place by the management. Ramos admitted he was shocked when he arrived to see the pastries, sweets and sauces on offer to the players at the club’s training ground. Such treats were immediately banned and the players were instructed to lose weight or lose their place in the team.

The approach was clearly paying off, with the likes of Huddlestone – known to be a big fan of ketchup – looking trimmer and more mobile than he ever had before. Jermaine Jenas and Malbranque looked to particularly benefit from the new manager’s more dynamic and aggressive attacking style of play, as the team racked up high-scoring wins over Reading (6-4) and Fulham (5-1).

The real marker of their progress would be in the bigger games, though. After a 1-1 draw at the Emirates in the first leg of the Carling Cup semi-final, Spurs faced their arch-rivals at White Hart Lane on 22 January with a first cup final appearance since 2002 at stake.

Ramos’ side got off to a flying start after Jenas put them ahead on three minutes and the home side were rampant throughout. The visitors couldn’t cope with the intensity of Spurs’ attack as they bombarded them with wave after wave of lightning-fast transitions. Aaron Lennon put the home side 4-0 on the hour mark following a Nicklas Bendtner own goal and a Keane strike that came just after the break. Emmanuel Adebayor got a consolation goal for the home side but Malbranque, who rarely stopped running, was on hand to put the icing on the cake and seal the 5-1 victory in injury time.

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A week later, they came close to beating Sir Alex Ferguson’s Manchester United. A superb team performance that saw them lead 1-0 for the majority of the game was undone as Carlos Tevez equalised from a corner in the fourth minute of injury time.

Despite the team’s impressive form, few expected them to get a result at Wembley against rivals Chelsea, who incidentally had also changed manager that season with Avram Grant replacing José Mourinho. All appeared to be going according to script as Didier Drogba scored from a free-kick to put the holders ahead in the 39th minute. Spurs were handed a lifeline in the second half, though, as the assistant referee spotted a handball by Wane Bridge in the area and Berbatov coolly slotted home from the penalty spot.

As the game went into extra-time, it was Woodgate who would be the unlikely hero as a Petr Čech clearance rebounded in off his head and into the net. On the final whistle, a tearful Keane brushed past his teammates to embrace his strike partner Berbatov. The pair were unstoppable together up front that season, causing Defoe to leave to seek more playing time at Portsmouth and limiting Bent to appearances off the subs’ bench.

The team looked set to push on to bigger and better things, and they still had a UEFA Cup last-16 tie against PSV to look forward to the following month. After losing the first leg 1-0 at White Hart Lane, Berbatov scored a late winner past an inspired Heurelho Gomes in Eindhoven to take the tie into extra-time. Spurs were to eventually miss out on penalties, going down 6-5 in the shootout after Pascal Chimbonda put his spot-kick wide.

With the cup competitions over and relegation no longer a threat, instead of pushing on to challenge for a place in the top half, the team somehow went on cruise control. From the remaining ten league games, Ramos’ side only managed two victories – which came against Portsmouth and Reading – as the 2007/08 season petered out and the club finished in 11th. If Ramos wanted more professionalism and commitment from his players, he certainly didn’t seem to be getting it as the summer holidays approached.

Going into the summer of 2008, the onus was once more upon Comolli to scour Europe and beyond for the right players to improve the squad ahead of the 2008/09 campaign. Dinamo Zagreb playmaker Luka Modrić was one of the first to sign at the beginning of the summer, alongside Giovani dos Santos and Gomes, who had impressed with his performances against Spurs in the UEFA Cup and would replace Paul Robinson.

It was a summer clouded by speculation that Berbatov would depart for Manchester United, but what did come as a surprise was the club’s decision to sanction Keane’s departure to Liverpool for £19m. With the Irishman having just turned 28, it made good business sense, but considering that Defoe had already left the club that January and Berbatov was likely to follow, there was a risk of Bent becoming the club’s only senior striker. It seemed that someone at the club was highly confident of the £16.5m investment coming good, in spite of an underwhelming 2007/08 campaign, in which he mustered just six league goals.

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Two days later, another curious deal was concluded as David Bentley arrived from Blackburn in a £15m deal. Bentley was, of course, a promising player at the time who had recently been called up by England, but since Spurs already had an accomplished right-winger in Lennon, the transfer didn’t seem to address any particular weakness in the squad.

Berbatov’s departure was finally confirmed as the transfer window slammed shut, with Frazier Campbell joining on loan from Manchester United as part of the deal. Roman Pavlyuchenko was brought in from Spartak Moscow as a more direct replacement and Vedran Ćorluka joined from Manchester City.

By the time the transfer window closed on 1 September, there was already cause for concern at the team’s league form. Despite securing a respectable 1-1 draw away at Chelsea in their third game, Ramos’ side had not been expected to lose both of the opening games, which saw them go down 2-1 to Middlesbrough and Sunderland respectively.

The new signings made little impact as Ramos chopped and changed from game to game. Gomes’ confidence was seriously affected after some early-season howlers; full-back Vedran Ćorluka ended up filling in at centre-half; and Modrić was either placed on the left or squeezed into the middle of a five-man midfield with Lennon and Bentley manning the flanks.

Ramos still struggled to speak English, with Poyet handling interviews on his behalf and it was clear that however the Spaniard was communicating with his players, the message wasn’t getting across. The team looked lost and demotivated. They failed to settle and the results got even worse. After a 2-1 defeat at Stoke on 19 October, the team had just two points from eight games, a statistic Harry Redknapp would subsequently be all too keen to remind journalists of at any given opportunity – and some not given as well.

With the club in the relegation zone, Levy called a meeting with senior players King and Jenas to get to the route of the problem. He was told in no uncertain terms that to sell Defoe, Keane and Berbatov without securing proper replacements was a foolish venture. Defoe and Keane would be brought back to the club in the next January transfer window, but Comolli and the manager he had brought in were given no second chances. On 25 October 2008, a year to the day since Jol’s sacking and 363 days after taking charge, Juande Ramos was sacked along with Poyet, Álvarez and Comolli.

Levy had decided to abandon the continental structure and do what all chairmen seem to do when a managerial appointment goes wrong: find a manager who is the complete antithesis of the guy you’ve just sacked. Enter stage Harry Redknapp.

By Gareth Thomas @gareththomas54