The draw of the Chibuku Super Cup First Round fixtures has seen Harare giants, Dynamos and Bulawayo heavyweights, Highlanders paired. Below is the full list of teams participating and the teams they were paired with.
- Chicken Inn v Manica Diamonds
- Black Rhinos v Telone/ Yadah
- Caps United v Harare City
- Ngezi Platinum v Mushowani/ Bulawayo Chiefs
- ZPC Kariba v Hwange
- Triangle United v Herentals
- Dynamos v Highlanders
Dates: 28-29 September 2019
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