Paulo Bento's men failed to make the most of their possession as a lack of invention coupled with stalwart defending from the visitors made for a drab affairPortugal lacked creativity as they were shut out by a resilient Macedonia side with the pair playing out a dour 0-0 draw in Leiria in Saturday's friendly.
Paulo Bento's men got their Euro 2012 preparations off to a stuttering start as they were stifled by the number of bodies that the visitors put behind the ball. The Macedonians did pose an occasional threat on the counterattack but Goran Pandev looked out of sorts in a disappointing day for forwards all round.
Portugal set out to control possession from the off but Macedonia remained disciplined and compact with the game's opening chance coming in the 11th minute. Cristiano Ronaldo struck a free kick sweetly on the right corner of the box but it lacked the dip to work the keeper.
The visitors looked dangerous on the break and after a few failed attempts, Pandev found one of his team-mates with a disguised pass to Stefan Spirovski. The midfielder broke into the box but dragged his shot wide of the far post.
The game was being played at a pedestrian tempo and with John Toshack's side staying compact it meant that space was minimal in the final third. Both Miguel Veloso and Helder Postiga saw long-range efforts miss the target and Ronaldo soon joined them when he failed to make a clean connection and curled the ball shy of the near post.
Macedonia continued to stifle the hosts with their resolute defending and once again it was a set piece that offered the chance to trouble the goalkeeper. Ronaldo was not put off by the 40-yard distance to goal and lashed a fierce shot narrowly over the bar five minutes before the break.
The pace of the game was raised early in the second half as Fabio Coentrao offered more of an outlet down the left while Ricardo Quaresma began to get the better of Yani Urdunov.
Portugal however still struggled to work a clear opening to shoot and could have gone behind after a lapse in concentration in defence. Vance Sikov was given a free header just before the hour mark but he could not keep his effort down.
The increased vigour of the hosts soon fizzled out and once again they were back to a relatively predictable style of play. Ronaldo tried to find the net after cutting in from the right flank on two separate occasions but his attempts went wide of either post.
Wholesale changes in the second half made no difference for Bento's side. Silvestre Valera added some dearly need width on the left which caused the visitors problems late on, but the finishing touch was lacking in what had been a very frustrating afternoon in front of goal.
Portugal will now play just one more friendly before the European Championship, which comes against Turkey next weekend and the coach will be eager for an improved performance.