Football Kenya Federation (FKF) partnered with SportPesa to unveil the 2019 SportPesa Shield on March 7, 2019. The tournament, which offers a KES 2 million prize pool and a pathway to the CAF Confederations Cup, revealed its round-of-32 fixtures during the launch event.
Matches will commence on March 16, 2019, with the final scheduled for June 1, 2019. The initial bracket includes clashes between 16 teams, featuring high-profile matchups such as Gor Mahia vs Kenpoly and AFC Leopards vs Transfoc.
- Fortune Sacco vs Wazito
- Uprising vs Western Stima
- Kenpoly vs Gor Mahia
- Kayo FC vs Bandari
- Congo Boys vs Kenya Police
- Emmausians vs Mwatate United
- Naivas vs Tusker
- SS Asad vs Ulinzi Stars
- Bungoma Super Stars vs Sofapaka
- Transfoc vs AFC Leopards
- Muranga Seal vs Kisumu All Stars
- Elim FC vs Kariobangi Sharks
- Trans Mara Sugar vs Bidco United
- Dero FC vs FC Talanta
- Vihiga Sportiff vs Ushuru
- Sindo United vs KCB
