Village Diamond
| Urusi | 3 - 3 | Village Diamond | 24/02/19 |
| Village Diamond | 1 - 0 | Sindo FC | 03/03/19 |
| Kobare Mobimba | 1 - 2 | Village Diamond | 16/03/19 |
| Hema Moja FC | 2 - 1 | Village Diamond | 17/03/19 |
| Village Diamond | 1 - 0 | Kamungei United FC | 23/03/19 |
| Kisumu City Stars | 2 - 2 | Village Diamond | 24/03/19 |
| Dero FC | 0 - 2 | Village Diamond | 07/04/19 |
| The Saints FC | 1 - 1 | Village Diamond | 13/04/19 |
| Lela FC | 2 - 2 | Village Diamond | 14/04/19 |
| Village Diamond | 4 - 2 | Kisumu Green Berets | 20/04/19 |
| Kibuye FC | 2 - 2 | Village Diamond | 21/04/19 |
| Village Diamond | 1 - 1 | Kapsoit FC | 27/04/19 |
| Kapkatet Youth FC | 2 - 1 | Village Diamond | 28/04/19 |
| Village Diamond | 3 - 1 | Marindi FC | 11/05/19 |
| Village Diamond | 4 - 1 | Kiplokyi FC | 12/05/19 |
| Village Diamond | 1 - 1 | Shauri Yako | 19/05/19 |
| Shauri Yako | 1 - 1 | Village Diamond | 02/06/19 |
| Kiplokyi FC | 0 - 2 | Village Diamond | 09/06/19 |
| Village Diamond | 4 - 0 | Kapkatet Youth FC | 15/06/19 |
| Kisumu Green Berets | 0 - 0 | Village Diamond | 23/06/19 |
| Kapsoit FC | 1 - 1 | Village Diamond | 30/06/19 |
| Village Diamond |
2 - 0
Suspended |
The Saints FC | 07/07/19 |
| Marindi FC |
0 - 2
Suspended |
Village Diamond | 13/07/19 |
| Village Diamond | 4 - 1 | Kobare Mobimba | 14/07/19 |
| Village Diamond | 1 - 1 | Urusi | 21/07/19 |
| Sindo FC | 3 - 0 | Village Diamond | 28/07/19 |
| Village Diamond | 2 - 2 | Lela FC | 10/08/19 |
| Village Diamond |
2 - 0
Suspended |
Hema Moja FC | 11/08/19 |
| Kamungei United FC |
2 - 0
Walkover |
Village Diamond | 17/08/19 |
| Village Diamond | 2 - 0 | Kisumu City Stars | 18/08/19 |
| Village Diamond |
2 - 0
Walkover |
Kibuye FC | 24/08/19 |
Dero FC
| Dero FC | 1 - 1 | Kisumu Green Berets | 24/02/19 |
| Kamungei United FC | 5 - 1 | Dero FC | 03/03/19 |
| Lela FC | 4 - 1 | Dero FC | 10/03/19 |
| The Saints FC | 1 - 2 | Dero FC | 17/03/19 |
| Kobare Mobimba | 2 - 0 | Dero FC | 24/03/19 |
| Dero FC | 0 - 2 | Village Diamond | 07/04/19 |
| Dero FC | 0 - 0 | Hema Moja FC | 13/04/19 |
| Dero FC |
2 - 0
Walkover |
Kiplokyi FC | 14/04/19 |
| Marindi FC | 0 - 1 | Dero FC | 21/04/19 |
| Dero FC | 2 - 1 | Kapkatet Youth FC | 27/04/19 |
| Shauri Yako | 2 - 1 | Dero FC | 28/04/19 |
| Urusi | 1 - 2 | Dero FC | 04/05/19 |
| Sindo FC | 2 - 0 | Dero FC | 05/05/19 |
| Kisumu City Stars | 5 - 0 | Dero FC | 11/05/19 |
| Dero FC | 2 - 1 | Kibuye FC | 12/05/19 |
| Dero FC | 1 - 0 | Kapsoit FC | 19/05/19 |
| Dero FC | 0 - 1 | Sindo FC | 02/06/19 |
| Kibuye FC | 1 - 1 | Dero FC | 09/06/19 |
| Dero FC | 1 - 1 | Shauri Yako | 15/06/19 |
| Dero FC | 2 - 2 | Urusi | 16/06/19 |
| Kapkatet Youth FC | 3 - 0 | Dero FC | 30/06/19 |
| Hema Moja FC |
2 - 0
Walkover |
Dero FC | 07/07/19 |
| Dero FC | 1 - 1 | Kisumu City Stars | 13/07/19 |
| Kisumu Green Berets | 1 - 1 | Dero FC | 21/07/19 |
| Dero FC |
2 - 0
Suspended |
Marindi FC | 27/07/19 |
| Dero FC |
3 - 1
Abandoned |
Kamungei United FC | 28/07/19 |
| Dero FC | 3 - 1 | Lela FC | 04/08/19 |
| Kiplokyi FC | 2 - 1 | Dero FC | 10/08/19 |
| Dero FC |
2 - 0
Suspended |
The Saints FC | 11/08/19 |
| Dero FC | 0 - 0 | Kobare Mobimba | 18/08/19 |
| Kapsoit FC |
2 - 0
Walkover |
Dero FC | 25/08/19 |
Village Diamond prematch form
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Dero FC prematch form
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