The Buccaneers will be facing Sekhukhune United for the fourth time this season, having defeated them in a league fixture and over two-legs of the MTN8 semi-finals without conceding a goal.
Meanwhile, Masandawana were also drawn to play Golden Arrows for the fourth occasion after winning the last two clashes between them following their surprise 1-0 first leg MTN8 semi-final loss in Tshwane.
In-form AmaZulu are set to travel to battle a resurgent Stellenbosch while Kaizer Chiefs will be hosting an unpredictable Siwelele outfit.
Dates, venues and kick-off times are yet to be confirmed.
READ: CARLING KNOCKOUT: Kwayiba Brace Fires Stellenbosch FC to Victory Over Durban City
Carling Knockout Cup quarter-final draw:
Stellenbosch vs AmaZulu
Orlando Pirates vs Sekhukhune United
Kaizer Chiefs vs Siwelele
Mamelodi Sundowns vs Golden Arrows