The Telkom Knockout draw took place on Wednesday afternoon, with the two Soweto giants drawing opponents from the Western Cape.
The previous edition of the competition produced an unlikely winner in Baroka, who stunned overwhelming favourites, Orlando Pirates in the final held at the Nelson Mandela Bay Stadium in Port Elizabeth.
TKO draw: Mouth-watering fixtures in opening weekend
The opening fixtures are headlined by a clash between semifinals last time out, Kaizer Chiefs, who trek down to the coast for another encounter with 2016 champs, Cape Town City.
Amakhosi’s bitter foes, Orlando Pirates, on the other hand, have a date with top-flight newbies, Stellenbosch FC, who will travel to Orlando Stadium for their Telkom Knockout debut.
The Buccaneers will want to do one better than their last attempt at the crown, where they were beaten by Baroka in the final in Port Elizabeth.
Elsewhere, the defending champions kick off their title defence away from home, meeting 2014 winners and cup specialists Supersport United.
League champions, Mamelodi Sundowns – who last had their hands on the trophy in 2015 – will once again be on the hunt, and their begin their campaign at home to AmaZulu, while Bidvest Wits travel to Harry Gwala Stadium to take on Maritzburg United.
The 2019 Telkom Knockout kicks off on Saturday, 19 October with the final last 16 fixture taking place the following Monday.
Telkom Knockout fixtures
Highlands Park vs Black Leopards
Maritzburg United vs Bidvest Wits
Cape Town City vs Kaizer Chiefs
Mamelodi Sundowns vs AmaZulu
Supersport United vs Baroka
Orlando Pirates vs Stellenbosch FC
Golden Arrows vs Polokwane City
Chippa United vs Bloemfontein Celtic
2006: Silver Stars
2007: Kaizer Chiefs
2008: Ajax Cape Town
2009: Kaizer Chiefs
2010: Kaizer Chiefs
2011: Orlando Pirates
2012: Bloemfontein Celtic
2013: Platinum Stars
2014: Supersport United
2015: Mamelodi Sundowns
2016: Cape Town City
2017: Bidvest Wits