Jornada 1
| 14 Sep 14 |  Bodden Town |
2 - 2 |  Cayman Brac |
... |
| 15 Sep 14 |  Sunset |
0 - 1 |  Elite |
... |
| 15 Sep 14 |  Scholars |
1 - 2 |  Cayman |
... |
| 15 Sep 14 |  George Town |
0 - 2 |  Roma United |
... |
Jornada 2
| 28 Sep 14 | Roma United |
2 - 0 | Cayman Brac |
... |
| 29 Sep 14 | Cayman |
2 - 0 | George Town |
... |
| 29 Sep 14 | Bodden Town |
1 - 1 | Sunset |
... |
| 01 Oct 14 | Elite |
2 - 3 | Scholars |
... |
Jornada 3
| 05 Oct 14 | Elite |
5 - 1 | Cayman Brac |
... |
| 06 Oct 14 | Sunset |
0 - 3 | George Town |
... |
| 06 Oct 14 | Scholars |
2 - 2 | Bodden Town |
... |
| 06 Oct 14 | Cayman |
3 - 3 | Roma United |
... |
Jornada 4
| 12 Oct 14 | Cayman Brac |
0 - 4 | George Town |
... |
| 13 Oct 14 | Cayman |
1 - 3 | Sunset |
... |
| 13 Oct 14 | Elite |
3 - 2 | Bodden Town |
... |
| 13 Oct 14 | Roma United |
1 - 1 | Scholars |
... |
Jornada 5
| 19 Oct 14 | Cayman Brac |
2 - 7 | Cayman |
... |
| 20 Oct 14 | Roma United |
0 - 1 | Bodden Town |
... |
| 20 Oct 14 | George Town |
1 - 0 | Elite |
... |
| 20 Oct 14 | Scholars |
1 - 0 | Sunset |
... |
Jornada 6
| 26 Oct 14 | Cayman Brac |
1 - 3 | Sunset |
... |
| 27 Oct 14 | Roma United |
0 - 2 | Elite |
... |
| 27 Oct 14 | Bodden Town |
1 - 1 | Cayman |
... |
| 27 Oct 14 | George Town |
0 - 0 | Scholars |
... |
Jornada 7
| 02 Nov 14 | Scholars |
2 - 3 | Cayman Brac |
... |
| 02 Nov 14 | Sunset |
0 - 2 | Roma United |
... |
| 03 Nov 14 | Bodden Town |
2 - 0 | George Town |
... |
| 03 Nov 14 | Elite |
3 - 3 | Cayman |
... |
Jornada 8
| 16 Nov 14 | Cayman Brac |
1 - 1 | Roma United |
... |
| 16 Nov 14 | Scholars |
1 - 1 | Elite |
... |
| 16 Nov 14 | George Town |
1 - 4 | Cayman |
... |
| 23 Nov 14 | Cayman |
3 - 2 | Cayman Brac |
... |
Jornada 9
Jornada 10
| 30 Nov 14 | Scholars |
0 - 0 | Roma United |
... |
| 18 Dic 14 | Bodden Town |
1 - 2 | Elite |
2 |
| 04 Dic 14 | Sunset |
2 - 3 | Bodden Town |
... |
| 07 Dic 14 | Cayman Brac |
1 - 1 | Bodden Town |
... |
Jornada 11
| 07 Dic 14 | Roma United |
1 - 1 | George Town |
... |
| 08 Dic 14 | Cayman |
1 - 1 | Scholars |
... |
| 08 Dic 14 | Elite |
1 - 4 | Sunset |
... |
| 11 Dic 14 | Bodden Town |
1 - 0 | Roma United |
4 |
Jornada 12
| 14 Dic 14 | Cayman Brac |
1 - 3 | Elite |
... |
| 14 Dic 14 | George Town |
2 - 0 | Sunset |
... |
| 15 Dic 14 | Bodden Town |
1 - 4 | Scholars |
... |
| 15 Dic 14 | Roma United |
2 - 4 | Cayman |
... |
Jornada 13
| 18 Ene 15 | Sunset |
2 - 1 | Cayman Brac |
... |
| 19 Ene 15 | Elite |
1 - 1 | Roma United |
... |
| 18 Ene 15 | Scholars |
3 - 1 | George Town |
... |
| 19 Ene 15 | Cayman |
2 - 5 | Bodden Town |
... |
Jornada 14
| 03 May 15 | Bodden Town |
Apl | Cayman Brac |
... |
| 01 Feb 15 | George Town |
Apl | Roma United |
... |
| 02 Feb 15 | Scholars |
Apl | Cayman |
... |
| 04 May 15 | Sunset |
3 - 2 | Elite |
... |
Jornada 15
| 14 Feb 15 | Cayman Brac |
3 - 2 | Cayman |
... |
| 05 Mar 15 | Roma United |
1 - 1 | Bodden Town |
... |
| 16 Feb 15 | George Town |
1 - 2 | Elite |
... |
| 05 Mar 15 | Scholars |
1 - 1 | Sunset |
... |
Jornada 16
| 21 Feb 15 | Cayman Brac |
Apl | Sunset |
... |
| 22 Feb 15 | Bodden Town |
3 - 1 | Cayman |
... |
| 23 Feb 15 | Roma United |
1 - 1 | Elite |
... |
| 22 Feb 15 | George Town |
1 - 3 | Scholars |
... |
Jornada 17
| 01 Mar 15 | Roma United |
1 - 1 | Cayman Brac |
... |
| 01 Mar 15 | Bodden Town |
0 - 3 | Sunset |
... |
| 02 Mar 15 | Elite |
2 - 3 | Scholars |
... |
| 02 Mar 15 | Cayman |
1 - 0 | George Town |
... |
Jornada 18
| 15 Mar 15 | Elite |
0 - 2 | Cayman Brac |
... |
| 15 Mar 15 | Sunset |
1 - 0 | George Town |
... |
| 16 Mar 15 | Scholars |
4 - 0 | Bodden Town |
... |
| 16 Mar 15 | Cayman |
1 - 1 | Roma United |
... |
Jornada 19
| 22 Mar 15 | Cayman Brac |
1 - 3 | Scholars |
... |
| 16 Abr 15 | George Town |
1 - 1 | Bodden Town |
... |
| 23 Mar 15 | Roma United |
1 - 0 | Sunset |
... |
| 23 Abr 15 | Cayman |
3 - 3 | Elite |
... |
Jornada 20
| 19 Abr 15 | Cayman Brac |
5 - 1 | George Town |
... |
| 19 Abr 15 | Elite |
3 - 2 | Bodden Town |
... |
| 20 Abr 15 | Cayman |
4 - 3 | Sunset |
... |
| 20 Abr 15 | Roma United |
0 - 2 | Scholars |
... |
Jornada 21
| 01 Feb 15 | Scholars |
5 - 1 | Cayman Brac |
... |
| 01 Feb 15 | Bodden Town |
1 - 3 | George Town |
... |
| 01 Feb 15 | Sunset |
3 - 1 | Roma United |
... |
| 02 Feb 15 | Elite |
1 - 0 | Cayman |
... |