Having beaten Serbia 2-1 in a Euro 2016 qualifier on Sunday, Portugal coach Fernando Santos named a completely new starting XI for the friendly scheduled to raise money for the victims of a volcanic eruption on the Cape Verdean island of Fogo.
Despite the scratch side, Portugal will still have expected to see off Cape Verde - who were knocked out of the Africa Cup of Nations in the group stages - at Estadio Antonio Coimbra da Mota in Estoril.
But they were stunned by an impressive performance from Rui Aguas' side, who took the lead in the 38th minute as a seemingly aimless right-wing cross from birthday boy Odair Fortes was allowed into sneak into the net by debutant goalkeeper Anthony Lopes.
Gege's close-range strike doubled Cape Verde's advantage, and any prospect of a Portugal revival was effectively ended by Andre Pinto's 60th-minute dismissal.
Pinto saw red for hacking down Heldon as the Cape Verde forward raced clear of the defence, with Portugal unable to overcome their numerical disadvantage on a disappointing evening for Santos' men.
However, Portugal quickly began to dictate proceedings, with Cape Verde goalkeeper Vozinha called into action to keep out Vierinha's near-post header and then deny Bernardo Silva with a low stop.
But, against the run of play, Cape Verde took the lead as Lopes could only manage to get a hand to Fortes' cross-cum-shot, which looped in at the far post to delight the heavy contingent of fans supporting the islanders.
And they were given more to celebrate just five minutes later. Heldon's free-kick from the right-hand side of the box deflected into the path of Gege, who was presented with the simple task of tapping in from a yard out.
Portugal pressed to try to halve the deficit in the second-half restart, Hugo Almeida spurning a golden chance to pull a goal back as he headed wide from Vierinha's far-post cross.
But the hosts' hopes of mounting a comeback were dealt a major blow on the hour mark when Pinto was shown a straight red card for a reckless challenge as Heldon surged towards goal.
Pinto's sending off did not affect Portugal's attacking ambition, but their efforts ultimately proved fruitless on a famous night for Cape Verde.
