Portugal, losing finalists in 2004, will face outsiders Bosnia in their Euro 2012 play-off while Estonia take on the Republic of Ireland following Thursday's draw in Krakow, Poland.
In the other ties, 1996 runners-up the Czech Republic will take on Montenegro, who had only just achieved independence when the 2008 finals took place, and Guus Hiddink-coached Turkey will meet Croatia.
The first legs will be spread between November 11 and 12 with the returns all on November 15.
The Bosnians, who came within 13 minutes of automatic qualification and forcing France into the playoffs, will enjoy home advantage for the home leg.
But they will then have to negotiate a tough trip to Lisbon to face Cristiano Ronaldo and company as the eastern Europeans attempt to reach the finals for the first time.
Portugal, who lost out in their group to Denmark having started off with a 4-4 draw at home to no-hopers Cyprus, just edged out the same play-off opposition two years ago as they won both games 1-0 to advance to the 2010 World Cup finals in South Africa.
"I am not surprised by the way the draw has turned out," said Portugal coach Paulo Bento.
"We have a strong team and now we must concentrate on beating Bosnia. It is very important for us to do so. I am confident next year we shall be playing in Poland and Ukraine."
Former Polish international Zbigniew Boniek drew the names out of the hat.
The four play-off winners will join the 10 nations who went through automatically from the qualifying groups -- Germany, Russia, Italy, Holland, Sweden (as best runners-up), Greece, England, Denmark, holders Spain and France, as well as Poland and Ukraine who qualify as co-hosts.
Aljosa Asanovic, assistant manager of Croatia, admitted his team would have preferred a weaker play-off opponent.
"We are ready to play with Turkey, but I'm not happy about the draw result. For us it is a big game and I'm looking forward the final result," he said.
The draw for the finals will be held on December 2 in Kiev, with the finals starting on June 8 next year and running to July 1.
The 2012 finals will be the last to comprise 16 teams with the format being extended to 24 for the 2016 edition in France.
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