| 08 May 21 | r26        | Wazito FCWazito FC | - | KCBKCB |
| 08 May 21 | r26        | Kariobangi SharksKariobangi Sh | - | Mathare UnitedMathare Unite |
| 08 May 21 | r26        | Posta Rangers FCPosta Rangers | - | Ulinzi StarsUlinzi Stars |
| 09 May 21 | r26        | BandariBandari | - | Nzoia SugarNzoia Sugar |
| 09 May 21 | r26        | GOR MahiaGOR Mahia | - | HomeboyzHomeboyz |
| 09 May 21 | r26        | Western StimaWestern Stima | - | AFC LeopardsAFC Leopards |
| 09 May 21 | r26        | Zoo KerichoZoo Kericho | - | SofapakaSofapaka |
| 20 Jun 21 | r26        | Zoo KerichoZoo Kericho | - | Wazito FCWazito FC |
| 25 Jul 21 | r26        | Western StimaWestern Stima | 0 - 2 | Vihiga UnitedVihiga United |
| 25 Jul 21 | r26        | SofapakaSofapaka | 1 - 2 | HomeboyzHomeboyz |
| 26 Jul 21 | r26        | Ulinzi StarsUlinzi Stars | 1 - 0 | GOR MahiaGOR Mahia |
| 26 Jul 21 | r26        | Nairobi City StarsNairobi City | 1 - 2 | Bidco UnitedBidco United |
| 30 Jul 21 | r26        | KCBKCB | 0 - 2 | Posta Rangers FCPosta Rangers |
| 30 Jul 21 | r26        | Nzoia SugarNzoia Sugar | 4 - 1 | BandariBandari |
| 30 Jul 21 | r26        | Bidco UnitedBidco United | 1 - 0 | Western StimaWestern Stima |
| 31 Jul 21 | r26        | HomeboyzHomeboyz | 4 - 1 | Kariobangi SharksKariobangi Sh |
| 31 Jul 21 | r26        | AFC LeopardsAFC Leopards | - | GOR MahiaGOR Mahia |