| 29 May 21 | r29        | KCBKCB | 0 - 1 | SofapakaSofapaka |
| 29 May 21 | r29        | GOR MahiaGOR Mahia | - | BandariBandari |
| 29 May 21 | r29        | Mathare UnitedMathare Unite | - | Ulinzi StarsUlinzi Stars |
| 30 May 21 | r29        | Nzoia SugarNzoia Sugar | - | Wazito FCWazito FC |
| 30 May 21 | r29        | Western StimaWestern Stima | - | TuskerTusker |
| 30 May 21 | r29        | HomeboyzHomeboyz | - | Kariobangi SharksKariobangi Sh |
| 10 Jul 21 | r29        | Western StimaWestern Stima | - | Zoo KerichoZoo Kericho |
| 07 Aug 21 | r29        | Bidco UnitedBidco United | 1 - 1 | Ulinzi StarsUlinzi Stars |
| 07 Aug 21 | r29        | AFC LeopardsAFC Leopards | 3 - 1 | Vihiga UnitedVihiga United |
| 12 Aug 21 | r29        | Ulinzi StarsUlinzi Stars | 0 - 1 | AFC LeopardsAFC Leopards |
| 13 Aug 21 | r29        | Kariobangi SharksKariobangi Sh | 3 - 1 | Nzoia SugarNzoia Sugar |
| 14 Aug 21 | r29        | Wazito FCWazito FC | 0 - 3 | SofapakaSofapaka |
| 14 Aug 21 | r29        | Nairobi City StarsNairobi City | 2 - 2 | Posta Rangers FCPosta Rangers |
| 18 Aug 21 | r29        | Wazito FCWazito FC | 1 - 0 | Western StimaWestern Stima |