14 September 2019
Sg. Premier League
14 Sep  
FT'
Tampines Rovers FC
3 - 3
Balestier Khalsa FC
FT'
Brunei Dpmm FC
3 - 0
Warriors FC
15 September 2019
Sg. Premier League
15 Sep  
FT'
Albirex Niigata Singapore FC
4 - 1
Young Lions FC
FT'
Geylang International FC
4 - 4
Hougang United FC
18 September 2019
Sg. Premier League
18 Sep  
18:45'
Albirex Niigata Singapore FC
? - ?
Balestier Khalsa FC
18:45'
Geylang International FC
? - ?
Warriors FC
18:45'
Home United FC
? - ?
Young Lions FC
19:15'
Brunei Dpmm FC
? - ?
Tampines Rovers FC