| 1. Round | 15/12/2018 | Nkana FC | - | Simba SC | 2:1 | ||||
| 1. Round | 23/12/2018 | Simba SC | - | Nkana FC | 3:1 |  |
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| Group D | 12/01/2019 | Simba SC | - | JS Saoura | 3:0 | |
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| Group D | 19/01/2019 | AS Vita Club | - | Simba SC | 5:0 | ||||
| Group D | 02/02/2019 | Al Ahly SC | - | Simba SC | 5:0 | ||||
| Group D | 12/02/2019 | Simba SC | - | Al Ahly SC | 1:0 | |
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| Group D | 09/03/2019 | JS Saoura | - | Simba SC | 2:0 | ||||
| Group D | 16/03/2019 | Simba SC | - | AS Vita Club | 2:1 | ||||
| Quarter-finals | 06/04/2019 | Simba SC | - | TP Mazembe | 0:0 | ||||
| Quarter-finals | 13/04/2019 | TP Mazembe | - | Simba SC | 4:1 |
Uganda