| 18 Dec 22 | r16        | Posta Rangers FCPosta Rangers | - | KCBKCB |
| 18 Dec 22 | r16        | Ulinzi StarsUlinzi Stars | - | Bidco UnitedBidco United |
| 18 Dec 22 | r16        | Kariobangi SharksKariobangi Sh | - | TuskerTusker |
| 07 Jan 23 | r16        | AFC LeopardsAFC Leopards | - | HomeboyzHomeboyz |
| 07 Jan 23 | r16        | Fortune SaccoFortune Sacco | P - P | TalantaTalanta |
| 07 Jan 23 | r16        | Kariobangi SharksKariobangi Sh | - | KCBKCB |
| 07 Jan 23 | r16        | Nairobi City StarsNairobi City | P - P | APS BometAPS Bomet |
| 08 Jan 23 | r16        | Nzoia SugarNzoia Sugar | - | Bidco UnitedBidco United |
| 08 Jan 23 | r16        | Posta Rangers FCPosta Rangers | - | TuskerTusker |
| 24 Feb 23 | r16        | Kariobangi SharksKariobangi Sh | 2 - 0 | SofapakaSofapaka |
| 25 Feb 23 | r16        | Nairobi City StarsNairobi City | 0 - 2 | Ulinzi StarsUlinzi Stars |
| 25 Feb 23 | r16        | Mathare UnitedMathare Unite | 1 - 0 | Wazito FCWazito FC |
| 25 Feb 23 | r16        | BandariBandari | 2 - 0 | Bidco UnitedBidco United |
| 25 Feb 23 | r16        | HomeboyzHomeboyz | 1 - 0 | Vihiga BulletsVihiga Bullet |
| 25 Feb 23 | r16        | TalantaTalanta | 0 - 0 | Nzoia SugarNzoia Sugar |
| 26 Feb 23 | r16        | KCBKCB | 0 - 1 | AFC LeopardsAFC Leopards |
| 26 Feb 23 | r16        | Posta Rangers FCPosta Rangers | 0 - 1 | TuskerTusker |
| 01 Mar 23 | r16        | Wazito FCWazito FC | 1 - 3 | Kariobangi SharksKariobangi Sh |
| 01 Mar 23 | r16        | Mathare UnitedMathare Unite | 2 - 1 | GOR MahiaGOR Mahia |
| 11 Mar 23 | r16        | Nairobi City StarsNairobi City | 1 - 1 | SofapakaSofapaka |