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.
Cape Verde made a lively start and went close in the 11th minute as Julio Tavares saw a close-range effort deflected wide following good work down the right from Fortes.
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.
