Saturday’s clash at Orlando Stadium will be Chiefs coach Gavin Hunt’s first-ever taste of the Soweto Derby and Orlando Pirates coach Josef Zinnbauer’s second.
The winner between the Soweto giants will face either Bloemfontein Celtic or defending champions SuperSport United in the final.
In the semi-finals, SuperSport start at home at Lucas Moripe Stadium on November 1, before visiting Celtic for the second leg at Dr Molemela Stadium six days later.
Kaitano Tembo’s SuperSport United saw off Tshakhuma Tsha Madzivhandila 3-2 to reach the semi-finals.
They face a Celtic side that performed arguably the biggest upset of the tournament so far after booting out favourites Mamelodi Sundowns 1-0.
All the MTN8 semi-finalists, however, have an opportunity to gear themselves up for weekend action as they have midweek Premier Soccer League (PSL) fixtures.
Before meeting Pirates, Chiefs travel to Port Elizabeth for a league date with Chippa United on Tuesday.
Hunt and his men arrive at Nelson Mandela Bay Stadium keen to recover from last weekend’s 3-0 defeat by Mamelodi Sundowns in their league opener.
The Soweto Derby will see Chiefs facing another traditional giant within seven days and a win over Chippa would boost morale in Amakhosi’s camp ahead of the Pirates showdown.
The Buccaneers, on the other hand, will warm up for Chiefs with a PSL clash against Stellenbosch at home on Wednesday.
After drawing 1-1 with AmaZulu last Saturday, beating Stellenbosch could psych up Josef Zinnbauer’s men for the Amakhosi challenge.
As for SuperSport United, they gear up for Celtic with a league encounter away at Golden Arrows on Wednesday.
Celtic visit Swallows FC first before remaining in Gauteng for the Matsatsantsa MTN8 date.