| 20 May 23 | r30        | BandariBandari | - | HomeboyzHomeboyz |
| 20 May 23 | r30        | Kariobangi SharksKariobangi Sh | - | Bidco UnitedBidco United |
| 20 May 23 | r30        | Nairobi City StarsNairobi City | - | TuskerTusker |
| 21 May 23 | r30        | Nzoia SugarNzoia Sugar | - | TalantaTalanta |
| 21 May 23 | r30        | SofapakaSofapaka | - | KCBKCB |
| 21 May 23 | r30        | Ulinzi StarsUlinzi Stars | - | Wazito FCWazito FC |
| 28 May 23 | r30        | Bidco UnitedBidco United | - | Ulinzi StarsUlinzi Stars |
| 28 May 23 | r30        | GOR MahiaGOR Mahia | - | Nzoia SugarNzoia Sugar |
| 28 May 23 | r30        | HomeboyzHomeboyz | - | Nairobi City StarsNairobi City |
| 20 Jun 23 | r30        | TalantaTalanta | 2 - 2 | Nairobi City StarsNairobi City |
| 21 Jun 23 | r30        | Nzoia SugarNzoia Sugar | 0 - 2 | KCBKCB |
| 21 Jun 23 | r30        | Mathare UnitedMathare Unite | 1 - 1 | Ulinzi StarsUlinzi Stars |
| 21 Jun 23 | r30        | Bidco UnitedBidco United | 0 - 1 | Wazito FCWazito FC |
| 21 Jun 23 | r30        | GOR MahiaGOR Mahia | 2 - 3 | HomeboyzHomeboyz |
| 21 Jun 23 | r30        | BandariBandari | 1 - 0 | Kariobangi SharksKariobangi Sh |
| 21 Jun 23 | r30        | TuskerTusker | 1 - 1 | Posta Rangers FCPosta Rangers |
| 25 Jun 23 | r30        | Nairobi City StarsNairobi City | 1 - 4 | GOR MahiaGOR Mahia |
| 25 Jun 23 | r30        | Posta Rangers FCPosta Rangers | 1 - 2 | BandariBandari |
| 25 Jun 23 | r30        | Kariobangi SharksKariobangi Sh | 0 - 1 | AFC LeopardsAFC Leopards |