League champions Benfica, with one eye on their Champions League clash with Galatasaray, struggled to overcome plucky non-league Vianense.
Carcela gave the Eagles the lead ten minutes before the interval but Coulibaly equalised in the 79th minute.
With extra-time looming it was left to centre-back Jardel to save Benfica’s blushes as he headed home from a corner in the last minute.
FC Porto won 2-0 away at Second Division Varzim thanks to goals from Tello and André André whilst Sporting Lisbon negotiated the short journey across town to win 4-0 at minnows Vilafranquense.
One of the biggest upsets was Penafiel’s 2-0 win over Primeira Liga outfit Vitória de Guimarães, whilst CD Aves put paid to Moreirense in a five-goal thriller.
The visitors took a 2-1 lead with two minutes left but Cássio levelled matters in stoppage time before Nélson Pedroso grabbed an extra-time winner for Second Division Aves.
Gil Vicente, currently riding high in the Second Division, took the scalp of Primeira Liga newcomers Tondela 2-1.
There were mixed fortunes for the four Algarve clubs with Portimonense winning 5-0 at non-league Pampilhosa and SC Farense edging home against the amateurs of little Rio Tinto, an Ubay Luzardo penalty ten minutes before the break separating the two teams.
Louletano found Second division promotion hopefuls GD Chaves too strong as they went down 5-0.
SC Olhanense entertained Europa League hopefuls Belenenses and lost a close fought tussle 1-0, but it could have been so different had Said converted a first-half penalty.
Ricardo Ribeiro, who was on-loan at Olhanense last season, pulled off a great save and in the dying moments of the game denied Murilo another golden opportunity.