| 09 Jan 21 | r09        | KCBKCB | - | Posta Rangers FCPosta Rangers |
| 09 Jan 21 | r09        | Nzoia SugarNzoia Sugar | - | Western StimaWestern Stima |
| 09 Jan 21 | r09        | Wazito FCWazito FC | - | GOR MahiaGOR Mahia |
| 10 Jan 21 | r09        | Zoo KerichoZoo Kericho | - | TuskerTusker |
| 10 Jan 21 | r09        | Kariobangi SharksKariobangi Sh | - | AFC LeopardsAFC Leopards |
| 10 Jan 21 | r09        | SofapakaSofapaka | - | Ulinzi StarsUlinzi Stars |
| 14 Jan 21 | r09        | GOR MahiaGOR Mahia | 3 - 1 | Mathare UnitedMathare Unite |
| 22 Jan 21 | r09        | Wazito FCWazito FC | 2 - 1 | Nzoia SugarNzoia Sugar |
| 22 Jan 21 | r09        | Mathare UnitedMathare Unite | 0 - 0 | BandariBandari |
| 23 Jan 21 | r09        | Zoo KerichoZoo Kericho | 1 - 2 | TuskerTusker |
| 24 Jan 21 | r09        | KCBKCB | 3 - 1 | Western StimaWestern Stima |
| 24 Jan 21 | r09        | Kariobangi SharksKariobangi Sh | 0 - 2 | AFC LeopardsAFC Leopards |
| 30 Jan 21 | r09        | Nairobi City StarsNairobi City | 1 - 2 | Kariobangi SharksKariobangi Sh |
| 30 Jan 21 | r09        | Vihiga UnitedVihiga United | 1 - 1 | SofapakaSofapaka |
| 03 Feb 21 | r09        | Bidco UnitedBidco United | 1 - 0 | Posta Rangers FCPosta Rangers |
| 04 Feb 21 | r09        | Vihiga UnitedVihiga United | 1 - 1 | Western StimaWestern Stima |
| 15 Jun 21 | r09        | TuskerTusker | 0 - 1 | Posta Rangers FCPosta Rangers |
| 25 Jun 21 | r09        | SofapakaSofapaka | 0 - 0 | Ulinzi StarsUlinzi Stars |