The Kenya Cup 2018/2019 season kicks off on Saturday 17th November. This 15s season welcomes a new Broadcasting Partner, Bamba Sports, who will be airing two matches every Saturday. The introduction of this broadcasting partner means that there will be a double header every weekend from the 17th of November to the end of the regular season.
All the play off matches will be played at the same venue to enable Bamba Sports to air them.
The approved Double headers for the 2018-2019 season are as follows.
| Date | Fixture | Host | Host Venue | Time |
| 17-Nov -18 | HBR v Nondies | KCB | RFUEA | 2:00pm |
| KCB v Oilers | 4:00pm | |||
| 24-Nov-18 | Machine v Strath | Machine | KCB | 2:00pm |
| Nondies v KCB | 4:00pm | |||
| 01-Dec-18 | KCB v Mwamba | HBR | KCB | 2:00pm |
| HBR v Quins | 4:00pm | |||
| 08-Dec-18 | Machine v Impala | Quins | RFUEA | 2:00pm |
| Quins v KCB | 4:00pm | |||
| 15-Dec-18 | Nondies v Quins | Nondies | KCB | 2:00pm |
| KCB v HBR | 4:00pm | |||
| 12-Jan-19 | Quins v Nakuru | Quins | RFUEA | 2:00pm |
| Impala v Nondies | 4:00pm | |||
| 19-Jan-19 | Oilers v Strath | Oilers | Nakuru | 2:00pm |
| Nakuru v HBR | 4:00pm | |||
| 26-Jan-19 | Nondies v Machine | Impala | Impala | 2:0pm |
| Impala v Quins | 4:00pm | |||
| 09-Feb-19 | Mwamba v Blakblad | Kabras | RFUEA | 2:00pm |
| Quins v Kabras | 4:00pm | |||
| 16-Feb-19 | Nakuru v Oilers | Nakuru | Nakuru | 2:00pm |
| Kabras v HBR | 4:00pm | |||
| 23-Feb-19 | Impala v HBR | Impala | Impala | 2:00pm |
| KCB v Kabras | 4:00pm | |||
| 02-Mar-19 | Blakblad v Impala | Blakblad | KCB | 2:00pm |
| Nondies v HBR | 4:00pm | |||
| 16-Mar-19 | HBR v Mwamba | Mwamba | Impala | 2:00pm |
| Impala v Nakuru | 4:00pm | |||
| 23-Mar-19 | Blakblad v Machine | Strath | Impala | 2:00pm |
| Strath v Impala | 4:00pm | |||
| 30-Mar-19 | TBC | TBC | TBC | |
| 06-Apr-19 | TBC | TBC | TBC | |
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