Day one of the round of 16 saw last editions runner-up, Vipers SC, and fellow StarTimes Uganda Premier League side Soltilo Bright Stars FC qualify for the quarter finals.
Soltilo Bright Stars FC scored four goals past Buganda Regional League side Kiyinda Boys FC at Kavumba Recreational Ground. Ibrahim Kasinde scored a brace while Emmanuel Loki and Nelson Senkatuka scored the other two goals.
At the Kabaka Kyabaggu Stadium, Shariph Kimbowa scored the first goal five minutes after the start of the second half but Ashraf Mandela equalised for the visitors in the last fifteen minutes. The visitors, Vipers SC, went ahead to eliminate Wakiso Giants FC 3-4 after penalties were taken.
Teams qualified for the Quarter Finals
| Team | League |
| Vipers SC | StarTimes Uganda Premier League |
| Soltilo Bright Stars FC | StarTimes Uganda Premier League |
