| 1ªEliminatória | 04-11-2018 00:00 | Calipolense CDVV | 3 : 0 | Atlético SC Reguengos | |
| 04-11-2018 00:00 | SL Évora | 2 : 8 | SC Viana Alentejo | ||
| 04-11-2018 00:00 | Estrela FC V.Novas "B" | 1 : 2 | CF Estremoz | ||
| 04-11-2018 00:00 | CC Corval | 0 : 2 | Juventude SC "B" | ||
| 04-11-2018 00:00 | G União S Montemor | 2 : 7 | Lusitano GC "B" | ||
| 04-11-2018 00:00 | GD Portel | 0 : 7 | SC Borbense | ||
| 2ªEliminatória | 16-12-2018 00:00 | Lusitano GC "B" | 4 : 1 | Juventude SC "B" | |
| 16-12-2018 00:00 | SC Borbense | 6 : 0 | CCD Terena | ||
| 16-12-2018 00:00 | CF Estremoz | 3 : 0 | GDR Canaviais | ||
| 16-12-2018 00:00 | Calipolense CDVV | 2 : 0 | SC Viana Alentejo | ||
| Meias Finais | 10-03-2019 00:00 | CF Estremoz | 4 : 1 | Lusitano GC "B" | |
| 10-03-2019 00:00 | Calipolense CDVV | 1 : 4 | SC Borbense | ||