Republic's history of (mainly) play-off pain

Ireland face Estonia tomorrow in leg one of their duel to win a Euros place. But they have a bleak record with just one success in five attempts in the last 16 years. Jack Pitt-Brooke talks to some of the players who suffered – and those who enjoyed the solitary victory

Euro 1996: Ireland 0-2 Netherlands

On 13 December 1995, just 17 months after the 1994 World Cup, Jack Charlton's team faced Guus Hiddink's Netherlands. A place at Euro '96 was to be decided by a one-legged play-off, one of the last such occasions.

The venue, Anfield, was naturally a cradle of Irish support. "The stadium was mobbed with Irish," recalls defender Alan Kernaghan. John Aldridge, who started up front, remembered the atmosphere at his old ground as "second to none".

The two sides were in moving in opposing directions. Kernaghan describes it as "the point of no return" for Charlton's side, who had reached three of the last four major tournaments but which "was not a young team by any stretch of the imagination". The Netherlands, in contrast, were on a thrilling ascent. Thanks to Ajax's precocious 19-year-olds Clarence Seedorf and Patrick Kluivert, they were just too swift and too imaginative for Ireland. "Seedorf ran the show, he was tremendous," recalls Aldridge.

Kluivert converted Marc Overmars' cross to put the Dutch one up in the 29th minute, and chipped Alan Kelly late on to seal the win. The Irish were ransacked. "I came on as a sub for Denis Irwin, who'd had a tough game against Overmars," says Kernaghan. "My first tackle was a little bit rash, to say the least."

World Cup 1998: Ireland 2-3 Belgium (on aggregate)

Jack Charlton had been replaced by Mick McCarthy, who led Ireland to a two-legged play-off against Belgium in 1997 for a place at the 1998 World Cup in France. At Lansdowne Road, Denis Irwin's free-kick was equalised by Luc Nilis's masterful strike, leaving Ireland with the handicap of a first-leg score draw to overcome.

In Brussels, unpleasant weather spoiled any chance of good football. "It was raining, it was a horrible night," remembers midfielder Alan McLoughlin. "It was a bit of a dull game, there wasn't too much excitement. There was no ebb or flow because of the conditions."

Luis Oliveira put Belgium ahead, but after substitute Ray Houghton's equalising header, the Irish had the momentum. "I knew we were back in it," Houghton says. "I knew we were in with a chance." These Low Country opponents were not in the same category of quality as Guus Hiddink's Netherlands. "They were no better than us. I fancied our chances," Houghton admits.

Nilis, though, 20 minutes from time, tapped the winner past Shay Given. The Republic of Ireland would not play in their third consecutive World Cup. "After the game we were disappointed," says McLoughlin. Houghton and Andy Townsend, both veterans of the 1990 and 1994 World Cups, had played their last games for the side. "The door was closing on some of the older guys. You could just sense the ending of an era."

Euro 2000: Ireland 1-1 Turkey (aggregate, Turkey go through on away goals)

After the Belgium defeat, experience taught that a home win against Turkey in 1999 was vital. "It was up to us, we were at home first," says Denis Irwin. "You'd rather have it the other way round, with the home leg second. We knew we had to get a good result at home."

With 11 minutes remaining Robbie Keane, who had just signed for Coventry City for £6m, clipped Ireland into a vital lead. But they let it slip: Lee Carsley handled the ball, Tayfur Havutcu converted the penalty and Ireland were left in the same position as two years before.

Their task was even harder, as they were competing not in convenient Brussels but distant Bursa. "It was not the easiest for travelling," remembers Irwin. "Obviously they did it on purpose. We flew to Istanbul from Dublin, which took over four hours, then we had to take a coach down to a ferry, a really rocky ferry ride for over an hour, and then a coach for an hour and a half. They did everything possible to make it as uncomfortable as possible."

"We pressed again, we took the game to Turkey out there," says Alan McLoughlin, "but they were resolute." Ireland could not break through and Turkey were happy with their goalless draw which took them to the European Championship. "It wasn't enough to send us through," Irwin says of his final cap for Ireland. "It was a huge disappointment."

World Cup 2002: Ireland 2-1 Iran (on aggregate)

The miserable run ended in Iran. In qualification for the 2002 World Cup, Ireland finished second in their group, and of all the runners-up were drawn to face the third-placed Asian team. "The draw was kind to us," said midfielder Matt Holland, who played in both legs.

Ireland's form had been excellent, and the players were confident of winning a play-off at their fourth attempt. "We'd had a good campaign, a good group of players. I think we had belief," adds Holland.

At Lansdowne Road Ireland won 2-0, with goals from Ian Harte and Robbie Keane. They took that lead into the bear-pit of Tehran's Azadi Stadium, the largest and loudest in the Middle East. "It was one of the most amazing experiences at a match I'd ever been to," Holland remembers. "There were 120,000 people in the ground. The atmosphere was intimidating, there were things thrown at us on the pitch – bottles and fireworks – and one firecracker went off not far from Jason McAteer as we walked out on to the pitch."

A mature, disciplined display was enough to send Ireland through; it took Iran until the final seconds to break through and score the only goal of the match. But it was too little, too late to change the outcome.

"We were very professional in the match," says Holland, "it was a backs-to-the-wall performance, we were very solid, very difficult to break down." As they were in Iran, the Irish players celebrated by spraying each other with water rather than champagne.

World Cup 2010: Ireland 1-2 France (on aggregate, after extra time)

Ireland returned to the play-off stage in 2009 to face France. At Croke Park the French won 1-0 through a Nicolas Anelka goal, requiring an unlikely victory from Giovanni Trapattoni's team at the Stade de France. Robbie Keane gave the Irish the lead, and a ferocious defensive performance sent the tie into extra-time.

What happened then is well-known: Thierry Henry controlled a loose ball with his hand, before crossing to William Gallas who scored the decisive goal. In terms of drama and trauma in a World Cup play-off it is almost unmatchable. It was certainly horrendous luck for the Irish. It was as if all the pain and disappointment of the three lost play-offs in the 1990s had been condensed and compressed into a single shock.

"We were cheated," said Richard Dunne in the immediate aftermath, with a legitimate sense of injustice. "Fifa will probably be happy. Yet again the big decisions have gone for the bigger team."