Portugal leading top scorer and talisman, Cristiano Ronaldo missed a penalty for the second successive game as Portugal lost at home to Bulgaria in a friendly.
Marcelinho marked his debut by giving the visitors the lead in the first half, scoring from close range.
Portugal dominated virtually from the off, but were guilty of missing a string of chances as their Euro 2016 preparations suffered a blow.
Head coach Fernando Santos cut an often frustrated figure on the bench as his side failed to make the most of their almost complete dominance and the home fans made their feelings clear as they whistled their team off at the final whistle.
Ronaldo, who missed from the spot for Real Madrid against Sevilla on Sunday, saw his second-half penalty saved after Nikolay Bodurov’s handball.
Ronaldo’s spot-kick failure was not damaging for Real as his club side beat Sevilla 4-0 in La Liga but it did prove costly for his country as Portugal could not find a breakthrough despite having 30 shots on goal.