Even for Jack Charlton and the immortal Ireland team of the 1990s, the play-off for EURO 96 proved a step too far.
After a tough qualifying campaign saw them (just about) finish behind Portugal in their qualifying group and just ahead of Northern Ireland and Austria, the Republic of Ireland were ranked last of all the second-placed finishers from qualifying.
In those days, the six best group runners-up qualified automatically for the European Championships, with the bottom two playing a one-legged play-off to determine the final spot.
The task handed to Ireland was no easy one. The Netherlands were ranked seventh of the eight runners-up and, with the play-off at a neutral venue, the two sides set off for Anfield on December 13th 1995, with Ireland manager Jack Charlton hoping to work one last miracle.
He had, of course, brought Ireland to EURO 88, as well as two World Cups in 1990 and 1994 - we're going to assume you might be familiar with the events of Stuttgart, Genoa, Giants Stadium, etc.
At this stage, however, Ireland were a diminishing power. Ahead of USA 94 they had been ranked as high as sixth in the world - by the time of the play-off against the Dutch, they were in 21st. The Netherlands were tenth, making Ireland the underdogs at Anfield.
13 December 1995; Republic of Ireland's Tony Cascarino in action against Winston Bogarde (5) and Clarence Seedorf (4), Netherlands. European Soccer Championship Qualifying Play-off, Anfield, Liverpool, England. Photo by David Maher/Sportsfile
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To exacerbate the slowly growing gap between Ireland and the pinnacle of international football, two of their regular starters were ruled out of the play-off through injury, and another (Niall Quinn) was suspended.
Steve Staunton was, of course, a major absentee, but the unavailability of Roy Keane - on his way to a second double-winning season with Manchester United - was arguably far more significant.
Perhaps Staunton, Keane, and Quinn might have made a difference if they had been available. But a glance at the names on the Dutch teamsheet that night - van der Sar, Seedorf, Davids, Bergkamp, Kluivert, for a start - emphasises how much of an uphill task this was to begin with for Jack Charlton's Ireland.
The game played out largely as predicted. Goals in each half from Patrick Kluivert sealed a routine 2-0 win for the Netherlands, and Ireland were out. It would prove to be the final game Jack Charlton would manage for Ireland - and his summation of the emotional scenes after the game years later stand as a fitting testament to the special bond he enjoyed with the supporters of the Boys in Green.
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Beautiful interview captures special connection Jack Charlton had with Ireland
On this day in 1995, Jack Charlton managed his final game for Ireland, a 2-0 loss to the Netherlands at Anfield.
Here's Jack discussing the emotions of that night.
The sight of Jack being sent off to a chorus of 'You'll Never Walk Alone: goosebumpspic.twitter.com/wAOjyl8lSp— Balls.ie (@ballsdotie) December 13, 2022
Jack Charlton had made the impossible possible for Ireland. A country that had never reached a major tournament had not only done so under his watch, but reached the last eight of a World Cup and become a genuine power in the global game for over half a decade.
The Dutch had been in Ireland's group at EURO 88 and at Italia 90, and had knocked Charlton's team out of the last 16 at USA 94 - so there was perhaps something poetic about his last game coming against that opposition.
It wasn't a foregone conclusion before kick-off that Charlton would step aside but, in the aftermath of the Dutch play-off defeat, it was perhaps inevitable that the great man was set to step aside, with the team in decline and results wavering.
In an extraordinary and emotional scene, however, the Englishman who had dared Irish fans to dream for the best part of a decade was met with a cacophony of noise from the Ireland end. He was serenaded with a particularly poignant rendition of 'You'll Never Walk Alone,' even in spite of the result. It may not have been official that he was departing at that stage, but something in the air suggested that the Irish support knew that this would be their last chance to thank the man who had done so much for this team.
Years later, in a poignant interview with the late Jimmy Magee, Charlton recounted the warm reception he received that cold December night, and said that the deafening noise of the Irish fans in the face of such a disappointing result not only touched him personally, but summed up what made the Irish support so special:
We lost the game 2-0. For me, the Dutch on the night...we'd hardly made a chance in the game. You've got to expect it.
I went in to the players and we just sat in the dressing room and were getting changed. Somebody came and said to me, 'would you come back out on the pitch?'
I said, 'what for?' - and he says, 'the crowd won't go home.'
I went out on the pitch and everybody was there. Nobody had left. They were all singing, it was typical Irish. I couldn't believe that, after a result like that, when you haven't qualified, they would still stand there and sing and show their appreciation.
In all fairness, Jack, you could hardly have expected them to leave.
It would ultimately turn out to be the last game Jack Charlton managed at any level.
The memories of the Charlton era, already the pinnacle in the history of Irish soccer, are only more poignant in the years following his death in 2020. Even though Anfield 1995 didn't have a happy ending, it is perhaps more than any other occasion under Charlton the perfect summary of what he meant to the Irish fanbase - and what they meant to him.
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