Head to Head
| Antigua & Barbuda Premier Division | 2019/03/17 21:00 | Jennings Grenades v Old Road FC | L | 1-0 |
| Antigua & Barbuda Premier Division | 2018/12/16 21:00 | Old Road FC v Jennings Grenades | L | 0-3 |
| Antigua & Barbuda Premier Division | 2018/01/20 21:09 | Old Road FC v Jennings Grenades | L | 1-4 |
| Antigua & Barbuda Premier Division | 2017/11/26 23:00 | Jennings Grenades v Old Road FC | D | 1-1 |
| Antigua & Barbuda Premier Division | 2016/12/04 23:00 | Old Road FC v Jennings Grenades | L | 2-3 |