Head to Head
| Antigua & Barbuda Premier Division | 2019/01/27 21:00 | Five Islands v Old Road FC | L | 0-1 |
| Antigua & Barbuda Premier Division | 2019/01/06 21:05 | Old Road FC v Five Islands | L | 3-1 |
| Antigua & Barbuda Premier Division | 2018/02/11 21:00 | Five Islands v Old Road FC | W | 2-0 |
| Antigua & Barbuda Premier Division | 2017/12/02 21:06 | Old Road FC v Five Islands | W | 1-3 |
Home History
| Antigua & Barbuda Premier Division | 2019/12/29 21:00 | Jennings Grenades v Five Islands | W | 0-2 |
| Antigua & Barbuda Premier Division | 2019/12/21 21:00 | Liberta SC v Five Islands | L | 4-0 |
| Antigua & Barbuda Premier Division | 2019/12/15 21:01 | Five Islands v Pigotts Bullets FC | L | 0-1 |
| Antigua & Barbuda Premier Division | 2019/12/07 22:59 | Five Islands v Swetes FC | L | 0-5 |
| Antigua & Barbuda Premier Division | 2019/11/24 23:00 | Greenbay Hoppers FC v Five Islands | L | 2-1 |
| Antigua & Barbuda Premier Division | 2019/11/10 19:00 | Parham FC v Five Islands | W | 1-5 |
| Antigua & Barbuda Premier Division | 2019/11/03 21:06 | All Saints Utd FC v Five Islands | D | 1-1 |
| Antigua & Barbuda Premier Division | 2019/03/17 23:09 | Greenbay Hoppers FC v Five Islands | L | 5-1 |
Away History
| Antigua & Barbuda Premier Division | 2019/12/28 21:00 | All Saints Utd FC v Old Road FC | L | 1-0 |
| Antigua & Barbuda Premier Division | 2019/12/22 23:00 | Old Road FC v Pigotts Bullets FC | D | 1-1 |
| Antigua & Barbuda Premier Division | 2019/12/14 21:04 | Old Road FC v Ottos Rangers FC | W | 2-1 |
| Antigua & Barbuda Premier Division | 2019/12/08 20:58 | Old Road FC v Greenbay Hoppers FC | L | 2-6 |
| Antigua & Barbuda Premier Division | 2019/11/23 21:04 | Parham FC v Old Road FC | D | 0-0 |
| Antigua & Barbuda Premier Division | 2019/11/10 23:03 | Liberta SC v Old Road FC | W | 2-3 |
| Antigua & Barbuda Premier Division | 2019/11/02 22:59 | Old Road FC v Jennings Grenades | L | 1-2 |
| Antigua & Barbuda Premier Division | 2019/10/26 21:00 | Old Road FC v Swetes FC | L | 1-3 |