They are two mouthwatering clashes, with the fixture between Sundowns and Chiefs sure to grab the headlines, with those two sides having already played to a draw in the league this season.
Defending champions Pirates go to 2023 winners Stellenbosch, which will be no easy ride in the Cape Winelands.
Chiefs won through to the last four when they defeated Siwelele 2-1 on Sunday, while Stellenbosch left it late to oust AmaZulu.
Chiefs fell behind to an early goal from Siyabonga Ndebele but were awarded a penalty when Mfundo Vilakazi was upended in the box, only for Mduduzi Shabalala to put his spot-kick over the crossbar.
It was another nightmare from the spot among several for Chiefs this season and it was perhaps a surprise that leading scorer Wandile Duba did not take it.
When they were awarded a second spot-kick on the stroke of halftime after Shabalala was brought down in the box, Duba did step up and sent his shot down the middle and into the goal.
It was a seventh goal of the season for Duba, already his best campaign, and a fourth strike in the Carling Knockout, putting him ahead in the Golden Boot race.
Pule Mmodi and Dillan Solomons both flashed shots just wide of the post, but Chiefs did take the lead with seven minutes remaining.
Asenele Velebayi was played into space on the right and as the angle narrowed, he drilled the ball low past goalkeeper Jody February.
It is a first semi-final in the competition for Chiefs since 2019 as they look to lift the trophy for the first time in 16 years.
Zakhele Lepasa should have equalised for Siwelele with a minute left, but placed his shot wide of the far post.
Meanwhile, Sinoxolo Kwayiba scored a penalty with the last kick of the game as Stellenbosch defeated AmaZulu 2-1 in their Carling Knockout quarter-final at the Danie Craven Stadium.
Chumani Butsaka put Stellenbosch ahead in the first half, but the teams went into the break level after Gopolang Taunyana's own goal.
With time up on the clock, Stellenbosch were awarded a spot-kick and Kwayiba netted his fifth goal of the season for the club.
The result ended a run of six straight wins for AmaZulu dating back to August as they finally tasted defeat.
However, 2023 champions Stellenbosch are into the last four, completing a clean sweep of wins for the home sides in this year's quarter-finals.
Stellenbosch took the lead in the 28th minute following a fantastic volleyed strike from Butsaka.
Teenager Raoul Daniels provided a cross from the right and Butsaka met it on the volley under pressure from a defender, steering it goalwards and into the back of the net.
The lead lasted barely five minutes before AmaZulu equalised as Mondli Mbanjwa's shot deflected off the unfortunate Taunyana and into the net.
Mbanjwa swivelled in the box and his scuffed shot brushed the defender and trickled into the far corner of the net.
It was the first time new Stellenbosch goalkeeper Nathan Garrow had been beaten in a Stellies shirt, though it was just a second appearance for the New Zealander.
Both teams pushed for a winner in the second half and, in added time at the end of the game, the home side earned a penalty.
Kwayiba burst clear on goal, rounded the goalkeeper and saw his goal-bound shot blocked by the arm of Taariq Fielies. It was a clear penalty and the correct decision from the referee.