1st(1st leg) Tampines Rovers - Geylang International 2:0 (1:0)
2nd (2nd leg) Geylang International - Tampines Rovers 1:2 (0:1)
1st(1st leg): 26/10/2019 10:30 2nd (2nd leg): 30/10/2019 11:45 Winner: Tampines Rovers
1st(1st leg) Brunei DPMM FC - Warriors FC 1:0 (1:0)
2nd (2nd leg) Warriors FC - Brunei DPMM FC 4:2 (2:2, 4:3, 5:4) pso
1st(1st leg): 26/10/2019 10:30 2nd (2nd leg): 30/10/2019 11:45 Winner: Warriors FC