The Republic of Ireland will take part in their 10th play-off campaign when they resume their Euro 2020 quest in March next year.
Six of their previous bids have ended in failure, but it may come as some comfort to manager Mick McCarthy and his players that two of the last three have proved successful.
Ireland and Spain were pitched into battle when Syria withdrew from the tournament in support of African nations protesting over the allocation of places.
Each side won its home game and a decider was required with Jose Ufarte’s first international goal sending the Spaniards through on neutral territory in Paris.
Having sat out the finals in England 30 years earlier, Ireland were handed a chance to make make the short trip across the Irish Sea when they faced Holland in a one-legged showdown at Anfield.
However, Jack Charlton’s men succumbed 2-0 with a young Patrick Kluivert contributing both goals.
Denis Irwin’s early opener was not enough for Ireland to secure a home advantage after Luc Nilis ensured the Belgians returned to Brussels with a 1-1 draw.
Goals from Luis Oliveira and Nilis secured a 2-1 second-leg victory despite Ray Houghton’s strike as substitute David Connolly was sent off late on.
Ireland were unable to hang on to a first-leg lead once again as Tayfur Havutcu’s late penalty at Lansdowne Road cancelled out Robbie Keane’s effort.
That left McCarthy’s side up against it ahead of the trip to Bursa – and amid a row over the training facilities provided for the respective teams, the Turks fought out a 0-0 draw to book their ticket to Belgium and Holland for the finals.
Having missed out on automatic qualification to Portugal on goal difference despite taking four points from the Dutch, Ireland headed into unknown territory when they took on Iran over two legs.
Ian Harte’s penalty and a second goal from Robbie Keane sent them to Tehran in the driving seat and although they were without skipper Roy Keane, they held firm despite Yahya Golmohammadi’s stoppage-time strike.
Nicolas Anelka scored the only goal in Dublin as Ireland, already aggrieved at FIFA’s change of heart on seeding the play-off draw, turned in a disappointing display.
But the real controversy came four days later at the Stade de France when, with the visitors leading through Robbie Keane’s effort, Thierry Henry handled before crossing for William Gallas to equalise, but his offence was not spotted by the officials.
If Giovanni Trapattoni’s men had suffered ill fortune two years earlier, their luck changed markedly when Estonia were reduced to nine men in Tallinn with goals from Keith Andrews, Jonathan Walters and Robbie Keane’s double securing a 4-0 first-leg advantage.
A 1-1 draw in Dublin simply rubber-stamped the outcome.
Not so quiet now... pic.twitter.com/qO1mCGLuBh— FAIreland ⚽️🇮🇪 (@FAIreland) November 16, 2015
Robbie Brady’s late strike in a fog-bound Zenica looked to have given Martin O’Neill’s side the upper hand, but Edin Dzeko levelled the tie.
A first-half Walters penalty at the Aviva Stadium provided the impetus the home side needed and it was he who confirmed their place at the finals with a second 20 minutes from time.
A 0-0 draw in Copenhagen sent Ireland back to Dublin dreaming of a trip to Russia and when Shane Duffy headed them into an early lead, they appeared to have one foot on the plane.
However, the Danes, inspired by Christian Eriksen’s hat-trick, ultimately ran out 5-1 winners to deny them in brutal fashion.