| 23 Apr 21 | r23        | Posta Rangers FCPosta Rangers | - | Zoo KerichoZoo Kericho |
| 23 Apr 21 | r23        | AFC LeopardsAFC Leopards | - | Kariobangi SharksKariobangi Sh |
| 24 Apr 21 | r23        | Ulinzi StarsUlinzi Stars | - | Western StimaWestern Stima |
| 24 Apr 21 | r23        | KCBKCB | - | GOR MahiaGOR Mahia |
| 24 Apr 21 | r23        | SofapakaSofapaka | - | Nzoia SugarNzoia Sugar |
| 24 Apr 21 | r23        | TuskerTusker | - | Wazito FCWazito FC |
| 02 Jun 21 | r23        | BandariBandari | - | Zoo KerichoZoo Kericho |
| 26 Jun 21 | r23        | GOR MahiaGOR Mahia | 1 - 2 | Western StimaWestern Stima |
| 04 Jul 21 | r23        | BandariBandari | 1 - 1 | Nairobi City StarsNairobi City |
| 09 Jul 21 | r23        | Vihiga UnitedVihiga United | 0 - 2 | Wazito FCWazito FC |
| 10 Jul 21 | r23        | Ulinzi StarsUlinzi Stars | 0 - 2 | Nairobi City StarsNairobi City |
| 10 Jul 21 | r23        | HomeboyzHomeboyz | 4 - 2 | Mathare UnitedMathare Unite |
| 11 Jul 21 | r23        | Bidco UnitedBidco United | 0 - 0 | SofapakaSofapaka |
| 16 Jul 21 | r23        | TuskerTusker | 2 - 0 | AFC LeopardsAFC Leopards |
| 17 Jul 21 | r23        | Nzoia SugarNzoia Sugar | 1 - 2 | HomeboyzHomeboyz |
| 17 Jul 21 | r23        | Western StimaWestern Stima | 1 - 2 | Ulinzi StarsUlinzi Stars |