| h2h | 2023-10-05 | Pontassolense |  | 11:00 |  | Nacional B | J1 | FF | |
| h2h | 2023-10-05 | CD Barreirense B |  | 11:00 |  | Est. Calheta B | J1 | FF | |
| h2h | 2023-10-05 | Juventude de Gaula |  | 11:00 |  | AD Vermelhimponente C | J1 | FF | |
| h2h | 2023-10-05 | CF Caniçal |  | 11:00 |  | Camacha | J1 | FF | |
| h2h | 2023-10-05 | Est. Calheta B | | 11:20 |  | Santacruzense | J2 | FF | |
| h2h | 2023-10-05 | CF Caniçal | | 11:20 | | Pontassolense | J2 | FF | |
| h2h | 2023-10-05 | Camacha | | 11:20 | | Juventude de Gaula | J2 | FF | |
| h2h | 2023-10-05 | Nacional B | | 11:20 | | AD Vermelhimponente C | J2 | FF | |
| h2h | 2023-10-05 | Juventude de Gaula | | 11:40 | | CD Barreirense B | J3 | FF | |
| h2h | 2023-10-05 | AD Vermelhimponente C | | 11:40 | | Est. Calheta B | J3 | FF | |
| h2h | 2023-10-05 | Camacha | | 11:40 | | Santacruzense | J3 | FF | |
| h2h | 2023-10-05 | Nacional B | | 11:40 | | CF Caniçal | J3 | FF | |
| h2h | 2023-10-05 | CD Barreirense B | | 12:00 | | AD Vermelhimponente C | J4 | FF | |
| h2h | 2023-10-05 | Est. Calheta B | | 12:00 | | Camacha | J4 | FF | |
| h2h | 2023-10-05 | Juventude de Gaula | | 12:00 | | Pontassolense | J4 | FF | |
| h2h | 2023-10-05 | Santacruzense | | 12:00 | | Nacional B | J4 | FF | |
| h2h | 2023-10-05 | CD Barreirense B | | 12:20 | | Santacruzense | J5 | FF | |
| h2h | 2023-10-05 | Nacional B | | 12:20 | | Camacha | J5 | FF | |
| h2h | 2023-10-05 | Pontassolense | | 12:20 | | Est. Calheta B | J5 | FF | |
| h2h | 2023-10-05 | Juventude de Gaula | | 12:20 | | CF Caniçal | J5 | FF |
