The Republic of Ireland take on Bosnia-Herzegovina in the first leg of their Euro 2016 qualification play-off in Zenica on Friday night.
Five of their seven previous attempts at making major finals via the play-off route have ended in disappointment, with the controversial handball by Thierry Henry which cost them a place at the 2010 World Cup in South Africa the most heartbreaking of all.
WORLD CUP 1966 v SPAIN
Syria's withdrawal from qualification led to a play-off with Spain after both sides had won their respective home fixtures. Jose Ufarte's first international goal for the Spaniards was enough to seal a 1-0 win in Paris, booking their place at the tournament in England.
EURO 96 v HOLLAND
Another chance to feature in England was missed when Jack Charlton's side lost 2-0 to Holland at Anfield. A budding young striker by the name of Patrick Kluivert scored both goals as the Dutch progressed and Charlton's reign as Ireland boss drew to a close.
WORLD CUP 1998 v BELGIUM
Denis Irwin's early strike in the home leg was cancelled out by Luc Nilis as the Belgians took a 1-1 draw back to Brussels.
There, goals from Luis Oliveira and Nilis were too much for Ireland who succumbed to a 2-1 defeat with Ray Houghton's goal coming in vain as substitute David Connolly was sent off late on.
EURO 2000 v TURKEY
Away goals would be the undoing of Mick McCarthy's side this time around as Tayfur Havutcu's late penalty at Lansdowne Road drew Turkey level after Robbie Keane had opened the scoring.
Against a background of anger and recriminations over the training facilities afforded to the respective teams, the second leg in Bursa ended 0-0 to send Turkey on to Belgium and Holland for the finals.
WORLD CUP 2002 v IRAN
Only a superior goal difference saw Portugal top their qualifying group ahead of Ireland, who were plunged into the play-offs again despite taking four points off Holland.
Iran were their opponents and they finally ended years of hurt as Ian Harte and Keane struck to give McCarthy's men a 2-0 lead to take to Tehran.
With skipper Roy Keane missing from the squad. Ireland endured a tense night but Yahya Golmohammadi's stoppage-time strike was not enough to deny the visitors their place in Japan and South Korea.
WORLD CUP 2010 v FRANCE
Unquestionably the most controversial of Ireland's long history of play-off disappointments.
Giovanni Trapattoni's side lost 1-0 at home but drew level in the Stade de France courtesy of Keane, only to see William Gallas score a hugely controversial goal in extra-time.
Henry provided the cross for his compatriot but had controlled the ball with his hand before doing so.
The offence went unseen by the officials and it was enough for France to qualify for South Africa, leaving the Irish at home once more.
EURO 2012 v ESTONIA
Unlike in previous years, Ireland all but sewed up qualification in the opening leg - this time winning 4-0 against nine men in Tallinn. Keith Andrews and Jonathan Walters struck for Trapattoni's side before Keane bagged a brace, meaning the 1-1 draw at the Aviva Stadium in the return leg was more than enough for them to reach the finals in Poland and Ukraine.
