The all-conquering (on the home front, anyway) Manchester City side of 2018-19 became the first in the history of the English game to sweep all three major domestic trophies in one season when they took the Premier League, FA Cup and Carabao (League) Cup.

There had been several assaults on ‘the treble’ in the past, but all had failed. Manchester United’s 1993-94 vintage came the closest as they took the Premier League and FA Cup ‘double’ while falling short in the final of the League Cup, then sponsored by Coca-Cola.

Similarly, a few other teams had had great seasons only to fall short in the final reckoning, but at least most had at least taken one of the three trophies on offer to ease their disappointment.

What though of the side that made all the running in all three competitions and yet ended the season empty-handed?

Here’s looking at you, Tottenham Hotspur 1986-87.

Background

In 1984, long-serving manager Keith Burkinshaw stepped down from the manager’s post at White Hart Lane, expressing dissatisfaction at the way the game, and in particular, Spurs was becoming more business-minded. Burkinshaw had enjoyed a successful spell in charge and had helped Tottenham to rise to the mantle of London’s top club by the time he left immediately following the club’s 1984 UEFA Cup success over Bruges.

Unable to tempt their first choice to become Burkinshaw’s successor, the Tottenham board decided to appoint from within. Alex Ferguson’s loss was thus Peter Shreeves’ gain, and the man who had been Burkinshaw’s right-hand man took over the reins.

A good 1984-85 season saw Spurs mount a title challenge that lasted until the early weeks of April before a Howard Kendall-inspired Everton side was finally able to shake them off.

Much was expected of the team for the 1985-86 season, but unfortunately Spurs flattered to deceive all season and a very disappointing 10th was the best Spurs could muster. Perhaps slightly harshly, Shreeves paid for this slipping back amongst the pack with the sack.

Enter David Pleat: The Season Begins

The search was on once again for a new manager and with Fergie presumably still not interested, Tottenham Chairman Irving Scholar instead approached his counterpart at Luton Town, David Evans, and asked for permission to speak to Luton’s manager, David Pleat.

Evans was far from willing to let Pleat go without a battle, and Pleat’s eventual departure from Kennilworth Road occurred with a fair bit of bad feeling on all sides.

Nevertheless, it was with Pleat in charge that Tottenham started the season against Aston Villa at Villa Park in front of a poor gate of 24,712.

In a sign of things to come for the season, Clive Allen was on fire as he scored a hat-trick in a 3-0 Spurs victory.

Two days later Allen scored again as Tottenham opened their home league programme with a 1-1 draw against Newcastle, and when a solitary Graham Roberts goal was sufficient to defeat Manchester City the following Saturday, Tottenham sat atop of the embryonic league table with seven points from three games.

Blessed with such talents as Ray Clemence in goal, Danny Thomas and Gary Mabbutt in defence, Paul Allen, Ossie Ardiles, Glenn Hoddle and Chris Waddle in midfield, as well as the resurgent Clive Allen up front, Pleat added to the ranks with some astute signings.

First, he raided his old club Luton for Mitchell Thomas and a few weeks later went north of the border to sign Richard Gough from Dundee United after the Tannadice club had refused to sell him to Scottish rivals, Rangers. Early in the season, Nico Claesen was signed from Standard de Liege, and finally, just before Christmas, Steve Hodge joined from Aston Villa.

The signings of Thomas and Gough, in particular, meant there was no longer room for the somewhat robust Graham Roberts, who took his own particular brand of subtlety (or lack of) to Ibrox as part of Graeme Souness’s ‘English Invasion’.

As he left Tottenham for the last time he did so with the farewell words of Pleat ringing in his ears.

“He’s kicked a few down here,” Pleat told the press, “and now he’s off to kick a few up there”.

Tottenham couldn’t maintain their exhilarating start to the season, and by the time November rolled around, they were down in mid-table. A good run in December and over the Christmas period saw Tottenham move into fifth.

By now the side was beginning to settle down and Pleat had introduced a foreign-style 4-5-1 system that gave both free rein to Glenn Hoddle’s mercurial talents in midfield and suited the goalscoring prowess of the lone striker, Clive Allen. With the arrival of Claesen and Hodge in midfield, Spurs now suddenly had more options than ever before.

A New Year Dawns: A League Cup Trilogy

As 1987 ticked off the first month or two in the calendar, Spurs started motoring. The early rounds of the League Cup had seen routine victories over Barnsley, Birmingham City and Cambridge City bring about an away quarter-final tie at West Ham.

28, 648 spectators turned up at Upton Park to see Clive Allen secure a 1-1 draw and so the two sides met again six days later in the replay at White Hart Lane.

Perhaps lulled into a false sense of security due to the relatively low gate at Upton Park first time round, Tottenham and the police were taken back by the almost capacity crowd of 41,995 that turned up for the replay – at least 10,000 of whom were amongst the travelling West Ham support. Serious overcrowding and poor crowd control that evening occurred and a major incident was only just avoided.

The Hammers were overcome by a flattering 5-0 scoreline and this set up a North London derby against Arsenal in the semi-final. The fact that the first leg was played just six days later meant that Spurs played no less than four London derbies in 12 days, as they had also met and demolished Crystal Palace 4-0 in the FA Cup in between the League Cup clashes with West Ham.

A solitary Clive Allen goal at Highbury meant that Spurs had one foot in the final. With the fifth round of the FA Cup safely reached and league form picking up all the time, Spurs supporters had reasons to be optimistic.

Five straight victories in the league in February in March, the last of which was at home to leaders Liverpool, had Tottenham tucked in sixth place in the league but with five games in hand on the Merseysiders.

Amid these league games, though, came the League Cup semi-final second leg against Arsenal. Played on a Sunday afternoon in front of a live TV audience Spurs looked to confirm what they hoped would be first of two trips to Wembley in the season.

When the sides left the field at half-time, it looked for all the world that it was ‘mission accomplished’ as yet another Clive Allen goal separated the two sides on the day and doubled Spurs’ aggregate lead to 2-0.

It was then that folklore and possibly urban myth takes over. So sure were Spurs that they had done the job that someone supposedly decided to play Chas and Dave’s ‘classic’ cup final record, “Ossie’s Dream” over the tannoy system.

So the story goes, rather than give a team talk George Graham simply opened the windows in the away dressing room and let the strains of “Spurs are on their way to Wembley” fill the silence. Duly motivated, Arsenal scored two second-half goals to turn the tie on its head and force a replay, also at White Hart Lane three days later.

Once again Spurs took the lead, and once again Arsenal came from behind to win. That all three goals were scored late in extra time before another dangerously overcrowded away end has led the tie to be remembered as being amongst the most famous of all North London derby clashes.

With their dreams of the treble now in tatters, Spurs were left to concentrate on the league and FA Cup.

Immediately after the league victory over Liverpool, a draw against Newcastle and a defeat back on Pleat and Thomas’s old Kenilworth Road stomping ground meant there was a widening gap at the top of the table, but back-to-back victories over Norwich and Sheffield Wednesday just about kept them in the hunt.

A poor run of just five points from the next five games, however, put the final nails in the coffin of Tottenham’s title aspirations.

FA Cup Heartbreak

At least they still had the FA Cup to play for, though. The 4-0 victory over Crystal Palace in the fourth round was sandwiched victories over Scunthorpe United and Newcastle, and so brought Spurs face-to-face with Wimbledon in the quarter-finals in yet another London derby.

A tight game in front of 15,636 at Plough Lane was settled by two goals in the closing minutes by Chris Waddle and a superlative free-kick from his singing partner-in-crime, Glenn Hoddle.

It was about this stage in the season that Waddle and Hoddle decided to venture into the world of pop music and released a single titled, ‘Diamond Lights’. As records by footballers went, it wasn’t the worst effort in history, but after peaking at number 12 in the charts it was an experiment nobody was keen to repeat.

Into the FA Cup semi-finals, and in one of the decisions that just make you shake your head in wonder, the FA decreed that Spurs’ clash with Watford would take place a hundred-and-twenty miles away at Villa Park rather than just around the corner at Highbury or down the road at Stamford Bridge.

This was the ‘Gary Plumley’ match in which Watford’s goalkeeper on the day was dragged in from part-time football and wine bar management to play the biggest game of his career following injuries to Watford’s two senior ‘keepers.

Unfortunately for Plumley, Graham Taylor’s gamble backfired spectacularly, and with Plumley at fault for at least three of the goals, Spurs prevailed by a 4-1 scoreline.

With Coventry City overcoming Leeds United in the other semi-final to reach their first-ever FA Cup Final, Tottenham at least had the chance to salvage something from a season that had once promised so much.

Red-hot favourites on a red-hot day, Spurs got off to a bad start with problems with their kit. Deciding to wear a new kit specially designed for the final, half the players made their way onto the Wembley turf with no sponsors’ logo adorning their shirts. Holsten, the company who sponsored Spurs at the time, was not amused and threatened to cancel their contract.

If Spurs were distracted by talk of sponsors and logos, once the game kicked off they showed no signs of being so. Clive Allen stooped after just two minutes to score his 49th goal of the season and Spurs were on their way.

Or were they?

Just six minutes later, Coventry’s Dave Bennett equalised and it was game on. Gary Mabutt restored Tottenham’s lead in the 40th minute and 2-1 to Spurs was the half-time score.

In the second half, the game ebbed and flowed in the Wembley sunshine and both sides spurned good chances before Keith Houchen scored one of the all-time great cup final goals. A Dave Bennett cross deep into the Spurs’ penalty area somehow evaded the white-shirted defenders and Houchen ghosted between them to equalise with a sublime diving header to force extra-time.

Five minutes into the extra period and Lloyd McGrath made progress down Coventry’s right flank. His aimed cross was in the general direction of Nick Pickering and Cyrille Regis when it glanced off Gary Mabbutt’s knee and spun crazily over the head of Ray Clemence and into the net for Coventry’s winner.

This closed the scoring and so, a season that at one point had offered the possibility of a clean sweep ended up producing nothing tangible in the way of silverware.

Yet, this particular Tottenham team is still remembered as being amongst the best footballing sides in the club’s history. It might not have won anything, but the style and panache in which they approached the 1986-87 season are recalled with fondness.

Alas, things fell apart quickly afterwards. The cup final was the last match in a Tottenham shirt for Glenn Hoddle, while Richard Gough, Ray Clemence and Ossie Ardiles played only a few more games the following season. Manager David Pleat also left the club early the next season following rather unfortunate revelations regarding his private life, and the dream was well and truly over.

For a short while, though, the light shone very brightly indeed.