This is the first time Pirates have won the dreaded shootout against their archrivals in six Carling Cup meetings that have gone to penalties.
Sifiso Hlanti skied his penalty, while Vincent Pule slotted his spot kick straight down the middle to ensure the Buccaneers advance to the final.
There was little to no spark in the highly anticipated encounter as both teams displayed poor ball-playing abilities on a wet surface following rainfall at the 90 000-seater arena.
But there was a moment of madness when Thapelo Xoki’s free-kick in the first half was palmed away from Amakhosi shot-stopper Brandon Petersen as the ball was curling towards goal.
Chiefs responded equally as Ben Motshwari was despatched by Khama Billiat and slotted a through ball towards Kgaogelo Sekgota.
Meanwhile Sundowns booked their place in the final of the Carling Black Label Cup with a comfortable 3-0 win over AmaZulu at the FNB Stadium on Saturday.
Goals from Cassius Mailula, Surprise Ralani and Haashim Domingo secured victory for the Brazilians, who will now face the winner between Kaizer Chiefs and Orlando Pirates in the second semifinal.
