| 08 Feb 21 | r16        | Ulinzi StarsUlinzi Stars | 2 - 2 | Western StimaWestern Stima |
| 27 Feb 21 | r16        | KCBKCB | - | Nzoia SugarNzoia Sugar |
| 27 Feb 21 | r16        | GOR MahiaGOR Mahia | - | Kariobangi SharksKariobangi Sh |
| 27 Feb 21 | r16        | TuskerTusker | - | Western StimaWestern Stima |
| 27 Feb 21 | r16        | Ulinzi StarsUlinzi Stars | - | Posta Rangers FCPosta Rangers |
| 27 Feb 21 | r16        | Wazito FCWazito FC | - | BandariBandari |
| 28 Feb 21 | r16        | Mathare UnitedMathare Unite | - | AFC LeopardsAFC Leopards |
| 28 Feb 21 | r16        | HomeboyzHomeboyz | - | Zoo KerichoZoo Kericho |
| 20 Mar 21 | r16        | Wazito FCWazito FC | 2 - 2 | BandariBandari |
| 03 Apr 21 | r16        | Ulinzi StarsUlinzi Stars | - | Bidco UnitedBidco United |
| 04 Apr 21 | r16        | Bidco UnitedBidco United | - | Zoo KerichoZoo Kericho |
| 25 Apr 21 | r16        | HomeboyzHomeboyz | - | Zoo KerichoZoo Kericho |
| 16 May 21 | r16        | Vihiga UnitedVihiga United | 0 - 0 | Mathare UnitedMathare Unite |
| 22 May 21 | r16        | Ulinzi StarsUlinzi Stars | 2 - 0 | Kariobangi SharksKariobangi Sh |
| 22 May 21 | r16        | HomeboyzHomeboyz | 4 - 0 | Western StimaWestern Stima |
| 23 May 21 | r16        | KCBKCB | 3 - 0 | BandariBandari |
| 23 May 21 | r16        | Nzoia SugarNzoia Sugar | 2 - 2 | Mathare UnitedMathare Unite |
| 24 May 21 | r16        | Nairobi City StarsNairobi City | 3 - 0 | SofapakaSofapaka |
| 23 Jun 21 | r16        | Mathare UnitedMathare Unite | 1 - 0 | AFC LeopardsAFC Leopards |
| 11 Jul 21 | r16        | KCBKCB | 2 - 2 | TuskerTusker |
| 13 Aug 21 | r16        | Nzoia SugarNzoia Sugar | 3 - 1 | Kariobangi SharksKariobangi Sh |