Home History
| Jamaica - Premier League | 2014/11/05 23:00 | Waterhouse v Tivoli Gardens | W | 3-0 |
| Jamaica - Premier League | 2014/10/19 20:30 | Reno FC v Waterhouse | W | 1-3 |
| Jamaica - Premier League | 2014/10/07 02:00 | Arnett Gardens v Waterhouse | D | 0-0 |
| Jamaica - Premier League | 2014/09/28 23:00 | Waterhouse v Harbour View FC | L | 1-2 |
| Jamaica - Premier League | 2014/09/23 02:00 | Humble Lions v Waterhouse | W | 0-1 |
| Jamaica - Premier League | 2014/09/18 23:00 | Waterhouse v Montego Bay Utd | W | 3-0 |
| CONCACAF - Taça dos Campeões | 2014/09/17 00:00 | Waterhouse v DC United | L | 1-2 |
| Jamaica - Premier League | 2014/09/07 20:30 | Barbican FC v Waterhouse | W | 0-1 |
Away History
| Jamaica - Premier League | 2014/10/26 20:00 | Boys Town v Reno FC | W | 1-0 |
| Jamaica - Premier League | 2014/10/21 02:15 | Tivoli Gardens v Boys Town | L | 2-1 |
| Jamaica - Premier League | 2014/10/14 02:15 | Boys Town v Arnett Gardens | L | 2-3 |
| Jamaica - Premier League | 2014/10/05 23:00 | Harbour View FC v Boys Town | L | 4-1 |
| Jamaica - Premier League | 2014/09/30 02:00 | Boys Town v Humble Lions | W | 2-0 |
| Jamaica - Premier League | 2014/09/21 20:30 | Montego Bay Utd v Boys Town | L | 4-0 |
| Jamaica - Premier League | 2014/09/14 20:30 | Boys Town v Barbican FC | D | 1-1 |