Head to Head
| Antigua & Barbuda Premier Division | 2023/03/11 20:00 | Five Islands v Old Road FC | L | 0-5 |
| Antigua & Barbuda Premier Division | 2020/02/02 19:00 | Old Road FC v Five Islands | L | 3-0 |
| Antigua & Barbuda Premier Division | 2020/01/04 21:00 | Five Islands v Old Road FC | L | 0-2 |
| 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 | 2023/04/26 00:00 | Greenbay Hoppers FC v Five Islands | L | 4-1 |
| Antigua & Barbuda Premier Division | 2023/04/18 00:00 | Ottos Rangers FC v Five Islands | L | 2-1 |
| Antigua & Barbuda Premier Division | 2023/03/11 20:00 | Five Islands v Old Road FC | L | 0-5 |
| Antigua & Barbuda Premier Division | 2023/03/06 23:00 | Five Islands v Tryum | L | 1-2 |
| Antigua & Barbuda Premier Division | 2023/02/26 22:00 | Five Islands v Greenbay Hoppers FC | D | 1-1 |
| Antigua & Barbuda Premier Division | 2023/02/18 20:00 | Five Islands v Swetes FC | L | 1-2 |
| Antigua & Barbuda Premier Division | 2023/02/11 20:00 | Jennings Grenades v Five Islands | L | 6-2 |
| Antigua & Barbuda Premier Division | 2023/02/05 00:00 | Liberta SC v Five Islands | D | 3-3 |
Away History
| Antigua & Barbuda Premier Division | 2024/05/05 00:00 | Old Road FC v Green City FC | W | 2-0 |
| Antigua & Barbuda Premier Division | 2024/04/28 22:00 | Old Road FC v Greenbay Hoppers FC | D | 4-4 |
| Antigua & Barbuda Premier Division | 2023/12/02 20:00 | Old Road FC v Empire FC | W | 3-2 |
| Antigua & Barbuda Premier Division | 2023/11/27 22:00 | Pigotts Bullets FC v Old Road FC | W | 2-5 |
| Antigua & Barbuda Premier Division | 2023/04/16 20:00 | Old Road FC v Willikies FC | W | 4-2 |
| Antigua & Barbuda Premier Division | 2023/04/09 20:00 | Old Road FC v Pigotts Bullets FC | D | 1-1 |
| Antigua & Barbuda Premier Division | 2023/03/11 20:00 | Five Islands v Old Road FC | W | 0-5 |
| Antigua & Barbuda Premier Division | 2023/03/03 23:00 | Swetes FC v Old Road FC | W | 1-5 |