Portugal must overcome a two-leg play-off against Bosnia and Herzegovina if they are to reach next year s European Championship finals.
The draw for the Euro 2012 qualifying play-offs took place in Krakow on Thursday, with Portugal, captained by Real Madrid star Cristiano Ronaldo, handed a challenging tie against Balkan opposition.
Bosnia finished just one point behind France in Group D of qualifying, with a late goal from Samir Nasri in the final game scuppering their hopes of an automatic berth in Poland-Ukraine.
The tie will be a replay of their 2010 World Cup play-off in November 2009, which Portugal won 2-0 on aggregate.
The Republic of Ireland received arguably the kindest tie, drawn to play against Estonia, who have never reached a World Cup or European Championship finals.
Estonia were 10 points behind Italy in Group C, but did finish ahead of Serbia and Slovenia to book their place in the play-offs.
The draw also paired Euro 2008 semi-finalists Turkey with Croatia, who defeated eventual finalists Germany in the group stage of the last tournament.
Finally, the Czech Republic, second to Spain in Group I, are set to face Montenegro, who ran England close in Group G.
The first-leg matches will take place on November 11 and 12, with all of the return fixtures to be played on November 15.
The draw for the tournament itself will be held on December 2 in Kiev.
The other teams already through to the finals are holders Spain, along with the Netherlands, England, Germany, Italy, France, Russia, Greece, Denmark and Sweden.
They will be joined by co-hosts Poland and the Ukraine, as well as the four play-off winners, with the tournament set to begin on June 8 in Warsaw.
