2. Round
20/09/2019 19:30 FCB Magpies - Europa FC Europa FC 0:6
22/09/2019 15:00 Europa Point FC Europa Point FC - Glacis United FC Glacis United FC 0:3
22/09/2019 17:15 Mons Calpe S.C. Mons Calpe S.C. - Lions Gibraltar Lions Gibraltar -:-
4. Round
19/08/2019 19:30 St. Joseph's FC St. Joseph's FC - College 1975 FC 7:0
21/08/2019 17:15 Europa Point FC Europa Point FC - Lynx FC Lynx FC 0:5
22/08/2019 19:30 Lincoln Red Imps Lincoln Red Imps - Glacis United FC Glacis United FC 8:0
23/08/2019 19:30 FCB Magpies - Lions Gibraltar Lions Gibraltar 2:0
29/09/2019 19:30 Boca Gibraltar Boca Gibraltar - Mons Calpe S.C. Mons Calpe S.C. -:-
5. Round
25/09/2019 19:30 Europa FC Europa FC - St. Joseph's FC St. Joseph's FC -:-
29/09/2019 15:00 Lions Gibraltar Lions Gibraltar - Lincoln Red Imps Lincoln Red Imps -:-
29/09/2019 17:15 Lynx FC Lynx FC - FCB Magpies -:-
30/09/2019 19:30 College 1975 FC - Manchester 62 FC Manchester 62 FC -:-
05/10/2019 15:00 Mons Calpe S.C. Mons Calpe S.C. - Europa Point FC Europa Point FC -:-