Winning is fun; it’s true, it’s true. What a moment to remember, what a thrill to enjoy! But let’s be honest, when the bones are boiled down, there’s never much left to sink your teeth into. And just as the devil has all the best tunes, so football’s beautiful losers boast the most romantic tales.

Ask the Brazil sides of 1950 and 2014, whose biblical failures ostensibly threaten to tarnish the country’s entire World Cup haul, but in fact make the story so much better in the telling. Ask last season’s Liverpool side, whose melodramatic widescreen capitulation (dir. Douglas Sirk) will be recalled in all its bittersweet glory long after many of the club’s actual titles have been forgotten. Ask Don Revie’s Leeds United, who in season 19 … actually, there are plenty to choose from there, though one in particular stands out.

Leeds United’s 1969-70 season is perhaps the single-most astonishing campaign in the history of English football. Revie’s team had, after years of striving, finally won the league title in 1968-69. With the monkey off the club’s back, the team buoyed by confidence and the oft-maligned Revie the new manager of the year, Leeds embarked on the following season in a mood to challenge on all fronts: the league, the FA Cup, the European Cup. It would be an unprecedented assault: only one team had won the league and Cup double in the last 70 years, never mind thrown a European title into the mix. It was surely impossible. It’s to Leeds United’s credit that, for a while, the impossible looked like it was on.

Leeds were hot favourites to retain their league title, starting the season as 11-4 favourites, with Everton and Liverpool at 7-1, Wilf McGuinness’s Manchester United 8-1, and Manchester City 10-1. By beating Tottenham Hotspur and Nottingham Forest, and drawing with Arsenal, they started the season by stretching their unbeaten run in league games to 31, breaking a record held by Burnley since 1921. Leeds “give the impression at the moment that they could climb Everest without oxygen”, opined the Observer of their brisk start.

Perhaps they did but it turned out a couple of their crampons were a little loose. Leeds failed to win any of their following five league matches, losing one of them to Harry Catterick’s increasingly impressive Everton. Integration of the newly signed Allan Clarke and the emerging Peter Lorimer wasn’t a totally smooth process, and by the turn of the calendar year Leeds had drawn 10 of their 27 league matches played.

They were only a point behind leaders Everton, but that early season inability to convert one point into two would eventually cost them. Leeds swanned to the semi-finals of both the FA Cup and European Cup – their debut in Uefa’s elite continental competition was a 16-0 aggregate win over Lyn Oslo – and a mid-season surge of form took them to the top of the table by early March. But injuries and a crowded fixture list – with the World Cup in Mexico coming up, the FA insisted that the season had to be completed before April was out – conspired to jigger Leeds on all fronts.

Billy Bremner’s goal in a second FA Cup semi-final replay against Manchester United booked a Wembley trip, but it was to be the last major celebration of the season. While Leeds had been away contesting that marathon semi, Everton had overtaken them in the league, and Revie – with Bremner, Terry Cooper, Johnny Giles, Norman Hunter, Mick Jones, Paul Reaney, Gary Sprake and Eddie Gray all carrying knocks – was forced to make a decision.

Eddie Gray was voted as the third greatest Leeds United player of all time by the club’s fans in 2000. Photograph: Evening Standard/Getty Images

His team were faced with an agenda that would simply not be tolerated today, and by clubs with far larger squads and sports science departments at that. Two days after overcoming Manchester United in the Cup Leeds entertained Southampton at Elland Road. Two days after that they travelled to Brian Clough’s Derby County. A further two days on and it was the visit of Jock Stein’s Celtic in the semi-finals of the European Cup. One day after that – one day! – and Leeds travelled to West Ham for a rearranged league fixture. Finally, after a luxurious two-day rest, Leeds entertained Burnley.

Including their Cup semi-final victory Leeds were to play six matches in 10 days. Little wonder the wheels came clanking off in a manner which owed a reasonable debt to the cinematic bombast of Ben Hur. Leeds were without six of their internationals against Southampton, but nevertheless deservedly went a goal up just after the hour through Lorimer. However, a ramshackle side could not hold it together and luck delivered Leeds a triple-whammy, straight in the chops: own-goals by Jackie Charlton and Terry Yorath and a penalty for what appeared to be a wholly accidental hand-ball by Terry Hibbitt. Saints became the first team to win at Elland Road in 39 matches, since Liverpool a couple of seasons before. The timing was hardly a coincidence.

Revie was at this point forced to accept the rearranged West Ham fixture. “The only conclusion to be drawn,” wrote the Guardian, “is that Leeds are willing to forgo the championship in order to strengthen their attempts for the FA and European Cups.” In reality, with the FA hell-bent on their pre-World Cup early finish, Leeds had little choice. Revie named a side of reserves for the fixture at Derby and were spanked 4-1. It was a double blow: the title was now as good as Everton’s, while the Football League were gearing up to fine Revie for his insolence, considering him in breach of a rule which stated that “each club shall play its full-strength team in all league matches unless some satisfactory reason is given”.

Revie had a comprehensive response prepared. “What is the point of employing the services of a fully qualified medical officer if you don’t take his advice? Our doctor declared that the players concerned were thoroughly tired, mentally and physically, and that, if they carried on, there was no knowing what damage might be caused. So we had no alternative but to take the steps we did. After all, the health of the players must be the first consideration of any club.

“I believe we were in with a chance of the championship until this massive congestion of fixtures. We could not have budgeted for two Cup replays with Manchester United for one thing, and in such heavy conditions. But when I saw the lads after that 120-minute battle with United in the first replay in the mud at Villa Park, I could have wept for them. They never complained but even Leeds can only take so much. I think it was then that we all realised that something would have to give.”

Leeds suffered heavy fixture congestion in 1969-70, not helped by a FA Cup semi-final replay against Manchester United. Photograph: Bob Thomas/Bob Thomas/Getty

An understandable decision, certainly a brave one. But much good it did them. What followed was an astonishing 48 hours of ill fortune. In the first leg of the European Cup semi against Celtic George Connelly’s first-minute shot, a strange half-hit spinner which threaded its way from the left-hand side of the box into the bottom-right corner of Gary Sprake’s goal, settled the match. An outrageous stroke of luck, although in fairness Celtic went on to dominate the game and ended deserved victors. Elsewhere that night, Everton were sealing the league title with a win at home to West Bromwich Albion.

The morning after the night before saw Revie, spiritually if not literally hungover, travel down to London early to cop a fine from the Football League. And in the evening, as Leeds drew 2-2 at West Ham, their right-back Reaney – who was looking forward to the FA Cup final, the second leg of the European Cup semi, and a place in England’s team at the World Cup – broke his leg. Revie had named Reaney in his starting XI only to placate the suits who had delivered the bollocking he’d received that morning.

And so to the final act of a dire week in which Leeds would play five times, losing the league, effectively losing the chance of making the European Cup final and losing one of their star players to serious injury. Revie, by way of exasperated response to this astonishing capitulation, named eight reserves in his side, a glorious two-stiff-fingered response to the powers that be.

And what a response from one of the star men he did name! In the 71st minute Peter Lorimer shot for goal. His effort was parried by Burnley’s goalkeeper Peter Mellor and picked up by Gray on the left-hand edge of the penalty area. Cue perhaps the most rococo jig in the entire history of association football, one which included two Puskas-esque pullbacks, two feints, a couple of jinks and a powerful no-backlift snapshot to score. Gray beat only (only!) four men in the sequence – Arthur Bellamy, John Angus, Eric Probert and Mike Docherty – though three of them were embarrassed twice with one, poor old Angus, sent skittering around on his impotent arsecheeks on both occasions.

As is usually the way with these things, a little serendipity fuelled the genius. In the build-up to the dribble, as Lorimer shot, Albert Johanneson was bundled to the ground and lay prone, clutching his knee. As a result, when Gray picked up the loose ball, he had no support nearby and so decided to go for it instead. It was something of a delicious irony that Johanneson inadvertently and indirectly influenced the goal. After starring in Leeds’ promotion season in 1963-64, and becoming the first black player to play in an FA Cup final a year later, he was edged to the periphery at Elland Road by a combination of injury, booze and the emergence of – yes, it writes itself – Gray. It proved to be Johanneson’s last appearance in a Leeds United shirt and something of a symbolic one.

Albert Johanneson, here training in front his Leeds teammates, played an indirect role in Gray’s second goal. Photograph: Evening Standard/Getty Images

Gray’s homage to Garrincha, an outrageous effort, quickly became part of Leeds United legend, though the same player had arguably scored an even better goal roughly an hour earlier, picking up a loose clearance near the centre circle on 10 minutes, turning and gently caressing a precision lob over Mellor from 40 yards. It was the player’s personal pick: dribbling was part of his everyday remit, he would argue, but manufacturing exquisite first-time shots from distance was never part of his usual repertoire. Gray’s astonishing dribble did not quite make it to the top of Revie’s chart, either. “The goal was one of the best I’ve seen since Eddie scored in an international youth tournament in 1966,” said Revie, who had clearly set the bar ludicrously high: “He beat eight men then. Today he only beat six.”

The most traumatic run of results in the history of the English game had been met with a blend of raw talent, exotic beauty and gritty defiance; how very Leeds. But while symbolically loaded, the 2-1 win was of little real consequence and would stand as the last hurrah in a season of doomed striving. In the FA Cup final Leeds came within four minutes of beating Chelsea, a team they had bulldozed 5-2 at Stamford Bridge earlier in the season, but conceded a scrappy equaliser. Celtic finished the job in the European Cup at Hampden. Then with a grim inevitability, Chelsea won the FA Cup final replay at Old Trafford, Gray’s butterfly genius crushed on Chelsea’s wheel, not least when Ian Hutchinson punched Gray in the business portion of his shorts.

And so concluded one of the most glamorous misadventures of all time. Leeds ended the season having failed on every front. English football was not quite ready for continent-wide success on this scale. Revie, with his league title bid crumbling around him, had suggested that any team landing a domestic league and Cup double plus European trophy would in effect be building “the eighth wonder of the world”; it was another 14 years before Liverpool landed a treble, another 29 before Manchester United achieved the treble. And yet Revie knew his team’s efforts had deserved at least a little something tangible.

“I’m very sick and very disappointed,” he admitted in the wake of the Cup final, just before cancelling a buffet reception for 400 people back in Leeds. “Here we are at the end of a hard season without anything to show for it. I’m sorry for my players more than for myself. They’re all absolutely dejected – you must be after going so close in three major tournaments – but they’ve got great character and they’ll be back on top next season.”

Leeds would in fact have to wait another three seasons before regaining their title but then trophies were not really the point of Revie’s team, whose repeated close shaves added to the mystique of one of English football’s most famous collectives. The grand collapse of 1969-70 was their most ill-fated odyssey of all but one destined to be remembered in a way the various successes of Everton, Chelsea, Celtic and Feyenoord will never be. It is a much better story, after all, and one embellished to perfection by Eddie Gray: a treble failure but with a signature double to die for.

• Thanks to Rob Bagchi, whose brilliant book The Unforgiven, co-authored with Paul Rogerson, is the definitive text on this most amazing of teams.