To borrow a line from the immortal Chas and Dave, in 1987 - with David Pleat's eleven, Tottenham Hotspur really were football's connoisseurs. As winter turned to spring that year, Pleat's scintillating side appeared on the cusp of emulating - perhaps even eclipsing - Bill Nicholson's legendary double winners. A League Cup semi-final had been reached against Arsenal. Spurs would soon be on their way to Wembley in the FA Cup. And the free-scoring Lilywhites were sufficiently well placed in Division One to elicit serious talk of a first top-flight title since 1961.

That the campaign ended without silverware and in an excruciatingly embarrassing tabloid scandal - precipitating Pleat's departure - will forever be a true Tottenham tragedy.

The first prize to fall was the League Cup. An epic semi-final went to a third game after Spurs’ hubris led to them throwing away a 2-0 aggregate lead going into the second half of the second leg at White Hart Lane. David Rocastle smuggled a soft injury-time winner, prompting David Pleat to declare it a “stab in the heart for Spurs.”

A happier outcome was achieved at the same stage of the FA Cup in the form of a comfortable 4-0 win over Watford at Villa Park. This time Spurs were on their way to Wembley. 

Tottenham's league form tailed off badly after that semi-final. They won only three of their final nine matches to finish the season third. The campaign's last two home games served only to illustrate what might have been. Oxford were beaten 3-1 in a match that saw Glenn Hoddle score his final goal in a Tottenham shirt: a splendid saunter from the halfway line rounded off with a delicious dummy on the keeper.

Tottenham travelled to Wembley as overwhelming favourites against unfancied Coventry. This despite the fact the Sky Blues had won 4-3 at Highfield Road in December when the sides had last met. Spurs, however, had been victorious in all seven of their previous FA Cup finals. Coventry were seeking the first major silverware of their 104-year history. Following the national anthem, the Tottenham players removed their tracksuit tops. Only then did right-back Chris Hughton notice something odd about Gary Mabbutt's shirt. It transpired that on five of the specially commissioned new Cup Final Hummel kits, the HOLSTEN logo was missing.

Despite this hiccup, Spurs looked destined to become the first team to win the FA Cup eight times when Clive Allen headed home from a Waddle cross inside two minutes. It was the striker's 49th strike of a magnificent season, setting a new club record along the way.

The lead lasted all of seven minutes. Keith Houchen used his aerial prowess to knock down a cross for Dave Bennett, who manoeuvred past Clemence before firing in from close range. The game was becoming an instant classic. Chances came and went at both ends. But it was Spurs who edged ahead again four minutes before half-time. Hoddle flighted a free kick into the Coventry area, which eluded three defenders before falling to Gary Mabbutt. The Spurs man appeared to just get the decisive touch ahead of Coventry skipper Brian Kilcline.

Coventry, however, would not be cowed and started the second-half on the front foot. Houchen was proving a menace. Gough and Mabbutt, who had played so well all season, could not cope. Just after the hour, Bennett escaped down the right flank and teased a low centre across the face of goal. Houchen had the run on Gough and plunged to send a diving header beyond Clemence. 2-2. It remains one of the most iconic FA Cup Final goals.

Neither side could find a winner in what remained of the match. And so Tottenham's Homeric season was extended by a further 30 minutes.

Coventry manager John Sillett would later say that he knew his side would win in extra time. Spurs had run out of puff. Their football, which had flowed so beautifully for nine months, now ran dry. Six minutes into the first half of extra-time, a stray Spurs pass presented possession to Rodger. He, in turn, worked the ball to McGrath on the right wing, who drove into the area and flashed a ball across goal. Mabbutt, guarding the near post, tried to cut it out but could only look on aghast as the ball deflected off his knee before looping agonisingly beyond Clemence.

There was to be no way back for Spurs. A season that promised so much would end with nothing. The recriminations began immediately on the Wembley pitch. Glenn Hoddle lamented, "it's a lot harder to paint a picture than it is to destroy one." While a tearful Richard Gough was overheard by his manager saying it was impossible to win trophies playing such quixotic football.

After the formalities, the players were bussed back to White Hart Lane. A giant canopy had been erected on the pitch with a stage. The anticipated victory party transformed into a wake. Gough and Pleat engaged in an open row, which ended abruptly when the defender stormed out. The next day the team were required to participate in an excruciating open-top bus parade before attending a reception at Harringay Town Hall.

For David Pleat, the torture was unrelenting, and about to get worse. In June, The Sun newspaper ran a front-page headline that read: SPURS BOSS CAUGHT CURB CRAWLING. The accompanying article detailed how, during his time at Luton, Pleat had been cautioned twice by police in three days for odd behaviour in a car park. However, with the support of chairman Irving Scholar, Pleat rode out the initial storm.

Adapting to life without Hoddle and Richard Gough, who had forced his way out of the club to join Rangers, Tottenham still managed to make a promising start to the 1987/88 season. Going into October’s North London Derby at White Hart Lane, Spurs had set a new club record of 14 consecutive home wins. Inevitably, Arsenal were to end that run in a match shown live on television, coming from behind to win 2-1. Many Arsenal fans in attendance that afternoon wore newly printed tee-shirts emblazoned with The Sun's front page about Pleat. At one point, several blow-up sex dolls were released from the away end, which a mischievous gust of wind carried around the pitch until stewards were able to tether them.

The timing of this reminder of Pleat's alleged indiscretion could hardly have been worse. Five days later, The Sun burned Pleat for a second time: SPURS BOSS IN VICE SWOOP AGAIN. Following a crisis meeting on the 23rd of October 1987, David Pleat resigned as Tottenham Hotspur manager. 

Paradise had been lost. 

Ewan Flynn is the author of When the Year Ends in One: How Tottenham Hotspur's 1991 FA Cup Win Saved the Club and Transformed English Football