John Aldridge says it will be fifth-time lucky for Republic of Ireland and they will finally reach a major tournament.
The former Liverpool striker believes Giovanni Trapattoni's men have been handed a golden opportunity to reach Euro 2012 after being paired with Estonia in Thursday's play-off draw.
The Irish have been knocked out of play-offs on four previous occasions, including their infamous clash with France before the 2010 World Cup when a controversial handball by Thierry Henry led to the goal that saw them eliminated.
But this time they were seeded and have been given the advantage of playing the second leg at their own Aviva Stadium on November 15.
And after avoiding potential clashes with Turkey, Bosnia-Herzegovina or Montenegro, Aldridge believes their luck has turned.
He told Sky Sports News HD: "There were some very good teams in there and you'd have to say Estonia was the one everyone wanted - and with the bonus of being at home in the second leg.
"They say it's swings and roundabouts and we've been very unlucky in previous play-offs, especially against France, and it's payback time.
"You can't take Estonia for granted because they've got the best team they've had in their short history.
"They've done exceptionally well to come second in their group and it will be tough, but it was probably the easiest of the four."
Estonia have never reached the finals of a major tournament, and this is Tarmo Ruutli's side's first play-off appearance.
And Aldridge, who represented the Republic at two World Cups and Euro 88, believes several members of Ireland's squad could be too old for the 2014 World Cup and so will be especially determined to play in Poland and Ukraine next summer.
"We haven't had the best of luck, but it's fifth time lucky," he continued.
"We've just got to take the opportunity because for some of the players it's their last opportunity to play on the big stage.
"The World Cup might be beyond some of the players who are getting to a ripe old age, so that will make it more interesting and make them more determined.
"You've got to be quietly confident. Estonia are a good side and you treat them with respect, but at the end of the day it's the draw everyone wanted and you've got to make sure you do the job in hand and get the results that you need.
"I think it will be fifth time lucky."
Their task will be made more difficult by continuing fitness doubts over star striker Robbie Keane and a suspension hanging over Kevin Doyle.
The Wolves man was sent off for an elbow in the Republic's last game against Armenia and UEFA are yet to rule on how long his ban will be.
Aldridge hopes he will only miss the first leg of the play-off, but is confident the likes of Shane Long, Simon Cox and Jonathan Walters will provide adequate cover.
He added: "We've got a few problems with Robbie Keane not being fit and Kevin Doyle being suspended, but we've got some decent players up front who can hopefully come in and do a real good job.
"Young Cox has done well, in particular, plus Shane Long and Walters. So there's a few lads who can come in and take the opportunity to show their value.
"It's a blow because in previous years Kevin and Robbie have been our best strikers and our most potent goalscorers, so it's not ideal, but it does create opportunities for other players to stake their worth.
"I thought Kevin was a little bit unlucky with the sending off and I just hope justice is done and he gets a one-match ban so he can play in the home leg.
"But Shane Long's done really well when he's deputised for either Robbie or Kevin, so it gives him a great opportunity."