| Date | Time | Home | Away | Matchday | Competition | ||||
|---|---|---|---|---|---|---|---|---|---|
| 2023-07-22 | Diamond Stars |  | 3-1 |  | Wilberforce Strikers | D34 | |||
| 2023-07-16 | Diamond Stars | | 1-0 |  | East End Lions | D33 | |||
| 2023-07-02 | Diamond Stars | | 2-1 |  | Real Republicans Freetown | D30 | |||
| 2023-06-11 | Diamond Stars | | 1-1 |  | Kamboi Eagles | D27 | |||
| 2023-05-17 | Diamond Stars | | 2-0 |  | Kallon FC | D26 |
