The 2018/19 Nedbank Cup Last 16 draw was conducted on Thursday with record champions Kaizer Chiefs pitted against The Magic.
Chiefs, who are the most decorated club in the history of the tournament with 13 titles, will be away to the ABC Motsepe League side.
The Magic stunned National First Division (NFD) outfit Maccabi FC in the round of 32, while Chiefs edged out ABC Motsepe League club Tornado.
Chiefs' Gauteng rivals, Bidvest Wits have been drawn against fellow Premier Soccer League (PSL) side Black Leopards, who will be at home.
Highlands Park will also face an all-PSL affair at reigning MTN8 champions Cape Town City.
TS Galaxy will be away to fellow NFD club Jomo Cosmos, who eliminated this season's Telkom Knockout Cup Baroka FC.
There will be an-all NFD affair when Cape Umoya United lock horns with Mbombela United at home.
Lamontville Golden Arrows will be hoping to avoid an upset when they travel to Mpumalanga Province where they are expected to face Witbank Spurs.
Bloemfontein Celtic will play host to NFD outfit Richards Bay, who knocked out the defending champions Free State Stars.
Lastly, Tshakhuma Tsha Madzivhandila will be hoping to eliminate another PSL club when they face Chippa United away having stunned Polokwane City in the previous round.
Dates, times and venues will be confirmed by the PSL in due course.
Full Fixture list:
Cape Town City v Highlands Park
Bloemfontein Celtic v Richards Bay
Black Leopards v Bidvest Wits
Chippa United v Tshakhuma Tsha Madzivhandila
Cape Umoya United v Mbombela United
Jomo Cosmos v TS Galaxy
Witbank Spurs v Golden Arrows
Magic FC v Kaizer Chiefs