Kwame Peprah scored the only goal of the game with a bullet header in the second half, and Pirates held defended the goal with their lives.
There was a sense of urgency from the Pirates players from the word go as they went into the encounter already trailing Simba.
However, they couldn’t score in the first half despite creating a number of good goalscoring chances with Peprah and Thembinkosi Lorch in the mix.
The second half was lively with Pirates pushing forward more and putting Simba under pressure in search of a goal.
Simba then found themselves a man down after striker Kope Mugalu was given a straight red card for a reckless challenge.
Pitates then got the breakthrough with Peprah finding the back of the net in the 60th minute, much to the delight of Pirates fans out in the stands.
The Buccaneers could have scored more had it not been for the two penalties that were denied even after VAR was put to use for verification.
Pirates also hit the crossbar in the closing stages of the game as they wanted to wrap up the game and book their place in the semi-finals.
In the end, the match had to be decided on penalties. Ofori was the hero as he saved a penalty and scored the winner.
HOW ORLANDO PIRATES LINKED UP VS SIMBA
Pirates XI: Ofori, Shandu, Maela, Ndah, Nyauza, Mabaso, Makaringe, Hotto, Lorch, Dzukamanja, Peprah.
Subs: Jele, Motshwari, Mhango, Ndlovu, T. Mabasa, Dlamini, Mosele.