Saturday’s game against Sunderland will be Sheffield United’s fifth playoff final. They have lost each of their previous four. I was at every one.1997, Crystal Palace 1-0 Sheffield United, Wembley: the one that hurtTechnically this was United’s second experience of playoff misery having lost a relegation playoff against Bristol City in 1988, but by the mid-1990s the Football League post-season had developed into A Thing, thanks in large part to the decision to move the final to Wembley in 1990.Having missed the 1993 FA Cup semi-final against Sheffield Wednesday – the true Year Zero of United’s Wembley misery – this was my first trip to the national stadium. Eight Ashdowns piled into a rented Ford Transit minibus and chugged down the M1, flags streaming from the windows and a makeshift “SUFC” scrawled in red electrical tape on the back.Hope was also a passenger, and with good reason. United had won 1-0 at Selhurst Park in December and Jan Åge Fjørtoft had inspired a confident 3-0 thumping in the return fixture at Bramall Lane in early April, six weeks before the final. We arrived in the Wembley car park before the team bus and had time for face-painting (not for me because, you know, I was 16) and a quick kick-about under the twin towers before roaring the team out in a cascade of red and white balloons.View image in fullscreen John Ashdown’s first trip to Wembley featured face paint for some of the family but nothing to smile about once the final started. Photograph: John Ashdown/The GuardianThat was the high point. Memory suggests we barely had a shot. Highlights suggest Palace didn’t either. But in the dying seconds David Hopkin looked to curl one … and I still can’t listen to Glad All Over without wincing.I remember very little about the ride home, other than it taking what felt like several months to get out of Wembley and someone – probably my dad – suggesting we’d comfortably “outballooned” the Palace fans, some elite-level straw-clutching that speaks to a lifetime of being a Blade.So a great day out but United didn’t really turn up. That would become a theme.2003, Wolves 3-0 Sheffield United, Millennium Stadium: the one that really hurtHope was in the air once more in 2003 at the end of a campaign that will for ever be known at Bramall Lane as the “Triple Assault” season. Strong Portsmouth and Leicester sides had romped away with the top-two places but Neil Warnock’s United had finished third, had been to the semi-finals of the FA Cup, denied by that David Seaman save at Old Trafford, and to the semi-finals of the Carling Cup, where they had beaten Liverpool at home and gone to extra time at Anfield. They were also coming into the playoff final on the back of one of the great Bramall Lane nights – the 4-3 semi-final win over Nottingham Forest.View image in fullscreen Hope was in the air once more in 2003 at the Millennium Stadium. Photograph: John Ashdown/The GuardianThe family made a weekend of it in south Wales. I travelled over from London for the day, the “no way am I getting my face painted” 16-year-old having matured into the “no way am I spending a weekend in Wales with my family” 22-year-old (they were both idiots).While in 1997 the misery had been a last-gasp dagger to the heart, this time it got stuck straight in: 1-0 down after six minutes, 3-0 down by half-time. I remember seeing the players physically slump after the second goal; following a season of so many backs-to-the-wall escapes and unlikely comebacks, there was an air, on and off the pitch, of “We just can’t do this again.” And we didn’t. That said, there’s still part of me that wonders what might have been if Michael Brown had scored his penalty at the start of the second half.2009, Burnley 1-0 Sheffield United, Wembley: the one I forget aboutI’m pretty sure Hope had left the building at this point. Six years on from the Triple Assault, Warnock had finally taken United up but failed to keep them there, leading to the disastrous Bryan Robson interregnum, before the line was restored by the appointment of Kevin Blackwell, Warnock’s former assistant.Looking back, it’s a wonder this United side made the playoffs, still less believable they went into the final day of the season with a chance of claiming an automatic spot. The plan of giving the ball to David Cotterill and hoping for the best had, to general surprise, largely worked, and a run-of-the-mill Preston had been dispatched with little drama and even less panache in the semi-finals. But by now a sense of doom was creeping in as Wembley approached.My abiding memory of the final is the weird floating club crest curtains that hovered over the pitch before the game. They seem to have been around before finals between 2008 and 2013, and created a strange dreamlike quality to proceedings. The memory of them makes me feel slightly sick.As for the match itself: Wade Elliott scored a screamer after 13 minutes and then nothing happened. So deeply forgettable was the game that no one in the family seems to remember who else was there, though I have a memory of me and my brother sitting there increasingly miserable as the inevitable played out. But in the grand scheme of things this a forgettable trauma, a sprained ankle amid the broken bones. Somehow the nadir was yet to come.2012, Huddersfield 0-0 Sheffield United; Huddersfield win 8-7 on pens, Wembley: the one where Steve Simonsen took a penaltyWhile other finals had provided a sort of Technicolour torture, this was concrete grey. A patched-up, impossible-to-love United team, Wembley at its soulless worst, a match that lives in the memory as having been played under glowering skies regardless of the actual weather. I’m told – and I had clearly blocked this out – that most of the Ashdown clan had crammed into my tiny north London flat before the game, which will have injected absolutely no bonhomie into proceedings.View image in fullscreen Watching Sheffield United in a playoff final has proved a futile exercise. Photograph: John Ashdown/The GuardianAnd, to no one’s great surprise, it was another futile afternoon – 90 minutes again Palace, 90 minutes against Wolves, 90 minutes against Burnley, and now 120 minutes against Huddersfield, and not only no goals but no sign of a goal, no hint of a goal, no suggestion of a goal.After the dourest 0-0 you’re ever likely to see, Neill Collins, in converting United’s second spot-kick in the shootout, did at least become the first United player to put the ball in the net at Wembley since Alan Cork in 1993, 19 years and almost seven hours of football earlier. But still there was new pain to be found. Huddersfield missed their first three penalties yet somehow United conspired to lose 8-7, goalkeeper Steve Simonsen blasting the 22nd and final spot-kick into the stratosphere.While Simonsen’s penalty blipped gently on Nasa’s radar on its journey into the far reaches of the solar system, disaffection stuck around, with United mired in League One and going nowhere. It would be four years, featuring playoff semi-final defeats by Yeovil and Swindon, before Chris Wilder finally shook the club to its senses.Which brings us neatly on to Saturday. It’ll feel very different – it was only when digging through old photos for this piece that it sunk in that this will be the first playoff final without my dad, who died in 2022. And for a variety of reasons, few other Ashdowns can make it. So it will be a flying visit, just me and my brother zipping down the M1 and back, no frills, no flags but, for the first time in a while, that familiar old feeling in the pit of the stomach that this might just be our year.
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