Portugal boast a squad with the likes of Cristiano Ronaldo and Nani, but they failed to qualify through the group stage and must now travel to the Balkans to face a Bosnia-Herzegovina side that very nearly edged out France to qualify from their group.
Portugal will have been disappointed not to have qualified from their group, a shocking 4-4 draw against Cyprus proving to be a particularly low point for a side that just last year beat world and European champions Spain.
Portugal, managed by Paulo Bento, have left Jose Bosingwa out of their squad, and, according to Goal.com, will be without the Chelsea defender for some time to come; he has ruled himself out of the side while Bento is manager.
Ricardo Carvalho walked out on the squad before the qualifier against Cyprus earlier this year and has announced his retirement from international football, leaving Portugal without one of Europe's top defenders.
The Portuguese will also be without midfielder player Danny and right-back Silvio, according to a report from Goal.com.
Bosnia-Herzegovina should not be underestimated. In Edin Dzeko, they have a striker in superlative form who is used to playing against the best Europe has to offer.
Asmir Begovic has put in some good displays for Stoke this season and has gained valuable European experience with the Premier League side.
Portugal are undoubtedly favourites; Ronaldo and Nani give Portugal the creative edge and with the likes of Pepe and Fabio Coentrao, they have some of Europe's top players.
Bosnia-Herzegovina are yet to qualify for a major tournament, but the men from the Balkans are used to punching above their weight; Portugal have a fight on their hands.
In the end, I believe Portugal will win out, despite the damaging effects of the infighting with manager Paulo Bento.
Predicted score over both legs: Portugal 4-3 Bosnia-Herzegovina.