And the result was effectively tied up after the first-leg as Robbie Keane scored twice in Tallinn while Jonathan Walters and Keith Andrews also found the net in a 4-0 victory.
Back in Dublin, qualification for Euro 2012 was confirmed with a 1-1 draw.
France, 2009
In Trapattoni’s first campaign as manager, Ireland were unbeaten after 10 qualifiers but still could only finish second to Italy in Group 8, having won just four games and scored 12 goals.
In the play-offs, the Irish were unseeded and faced into a potential clash with Portugal, Russia, Greece or France. They drew the latter and after a 1-0 loss in Croke Park, they faced a difficult task in the return fixture.
However, they conjured an excellent performance in Paris. Robbie Keane’s first-half goal forced the game to extra-time and we all know what happened next.
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Iran, 2001
Mick McCarthy’s side were superb in qualifying, led by the magnificent performances of Roy Keane in particular.
They could count themselves unlucky that automatic qualification wasn’t achieved, considering if was goal difference that separated them and Portugal in the end.
The other notable highlight of the qualifiers – a 1-0 win over Holland at Lansdowne Road – will live long in the memory as it ensured Ireland’s place in the play-offs at least.
They were randomly drawn to face the winners of the Asian Confederation play-off and that proved to be Iran.
So, in the first-leg, goals from Ian Harte and Robbie Keane secured a 2-0 win. Days later in Tehran, the Irish secured qualification to the World Cup, despite losing 1-0.
Turkey, 1999
Ireland were undone by eastern European sides as they tried to qualify for Euro 2000. They really should’ve finished top of Group 8 but two painful moments on the road cost them dearly.
The first came against Croatia in Zagreb when Davor Suker popped up with a 91st-minute winner.
Then in Skopje – a place with bitter memories anyway – Niall Quinn’s goal had Ireland in front against Macedonia until the last-minute when Stavreski scored with a free-header from a corner.
The draw meant another play-off and Ireland were drawn to face Turkey.
In Dublin, Robbie Keane scored with ten minutes left but moments later, Lee Carsley’s handball in the area resulted in Havutcu converting from the spot and giving the Turks a priceless away goal.
Four days later, on a terrible surface in Bursa, the Irish struggled for long periods and failed to find a goal.
Frustrations boiled over at full-time when Tony Cascarino clashed with a couple of Turkish players and fans.
Belgium, 1997
With Mick McCarthy in charge for his very first qualification campaign, the Irish were a side in transition and finished a long way behind Romania in Group 8.
In the play-offs, they faced Belgium but over two legs the Irish conceded three times – Luc Nilis grabbing two of those goals (one was an absolute peach), Luis Oliveira the other.
After a 1-1 draw in Dublin (and a fine Denis Irwin free-kick), there was brief optimism in Brussels when Ray Houghton cancelled out Oliveira’s opener. But Nilis grabbed Belgium’s second with twenty minutes to go and the Irish couldn’t find a leveller.
Holland, 1995
Jack Charlton’s aging crop of players ran out of steam as the qualification campaign for Euro ’96 came to a close.
There were four wins from the opening five games before that infamous scoreless draw in Liechtenstein. And then everything went off the rails.
Home and away defeats to Austria was the beginning of the end before the Irish were embarrassed by the sleek and silky Portuguese in Lisbon.
Ireland's recent play-off history not great but there are still reasons to be hopeful
IN THE LAST twenty years, the Republic of Ireland have seen their fair share of play-off ties.
There have been six in total and they’ve managed to win just twice.
Estonia, 2011
Giovanni Trapattoni’s charges finished second behind Russia in Group B and entered the play-offs as a seeded team.
They could’ve drawn Turkey, Bosnia or Montenegro but instead were paired with Estonia – the lowest ranked of the eight teams.
And the result was effectively tied up after the first-leg as Robbie Keane scored twice in Tallinn while Jonathan Walters and Keith Andrews also found the net in a 4-0 victory.
Back in Dublin, qualification for Euro 2012 was confirmed with a 1-1 draw.
France, 2009
In Trapattoni’s first campaign as manager, Ireland were unbeaten after 10 qualifiers but still could only finish second to Italy in Group 8, having won just four games and scored 12 goals.
In the play-offs, the Irish were unseeded and faced into a potential clash with Portugal, Russia, Greece or France. They drew the latter and after a 1-0 loss in Croke Park, they faced a difficult task in the return fixture.
However, they conjured an excellent performance in Paris. Robbie Keane’s first-half goal forced the game to extra-time and we all know what happened next.
Iran, 2001
Mick McCarthy’s side were superb in qualifying, led by the magnificent performances of Roy Keane in particular.
They could count themselves unlucky that automatic qualification wasn’t achieved, considering if was goal difference that separated them and Portugal in the end.
The other notable highlight of the qualifiers – a 1-0 win over Holland at Lansdowne Road – will live long in the memory as it ensured Ireland’s place in the play-offs at least.
They were randomly drawn to face the winners of the Asian Confederation play-off and that proved to be Iran.
So, in the first-leg, goals from Ian Harte and Robbie Keane secured a 2-0 win. Days later in Tehran, the Irish secured qualification to the World Cup, despite losing 1-0.
Turkey, 1999
Ireland were undone by eastern European sides as they tried to qualify for Euro 2000. They really should’ve finished top of Group 8 but two painful moments on the road cost them dearly.
The first came against Croatia in Zagreb when Davor Suker popped up with a 91st-minute winner.
Then in Skopje – a place with bitter memories anyway – Niall Quinn’s goal had Ireland in front against Macedonia until the last-minute when Stavreski scored with a free-header from a corner.
The draw meant another play-off and Ireland were drawn to face Turkey.
In Dublin, Robbie Keane scored with ten minutes left but moments later, Lee Carsley’s handball in the area resulted in Havutcu converting from the spot and giving the Turks a priceless away goal.
Four days later, on a terrible surface in Bursa, the Irish struggled for long periods and failed to find a goal.
Frustrations boiled over at full-time when Tony Cascarino clashed with a couple of Turkish players and fans.
Belgium, 1997
With Mick McCarthy in charge for his very first qualification campaign, the Irish were a side in transition and finished a long way behind Romania in Group 8.
In the play-offs, they faced Belgium but over two legs the Irish conceded three times – Luc Nilis grabbing two of those goals (one was an absolute peach), Luis Oliveira the other.
After a 1-1 draw in Dublin (and a fine Denis Irwin free-kick), there was brief optimism in Brussels when Ray Houghton cancelled out Oliveira’s opener. But Nilis grabbed Belgium’s second with twenty minutes to go and the Irish couldn’t find a leveller.
Holland, 1995
Jack Charlton’s aging crop of players ran out of steam as the qualification campaign for Euro ’96 came to a close.
There were four wins from the opening five games before that infamous scoreless draw in Liechtenstein. And then everything went off the rails.
Home and away defeats to Austria was the beginning of the end before the Irish were embarrassed by the sleek and silky Portuguese in Lisbon.
It was a similar story in a single-game play-off against Holland.
At Anfield, Patrick Kluivert scored twice as the Dutch eased to victory and put paid to Charlton’s time in charge.
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Euro 2016 Qualifiers Euro Vision Giovanni Trapattoni Jack Charlton Martin O'Neill Mick McCarthy Republic of Ireland