Home History
| Jamaica Premier League | 2014/11/09 23:00 | Waterhouse v Boys Town | D | 0-0 |
| 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 |
Away History
| Jamaica Premier League | 2014/11/25 01:30 | Cavalier v Waterhouse | L | 0-2 |
| Jamaica Premier League | 2014/11/09 20:00 | Reno FC v Cavalier | L | 1-0 |
| Jamaica Premier League | 2014/10/28 02:00 | Cavalier v Tivoli Gardens | L | 1-2 |
| Jamaica Premier League | 2014/10/20 23:30 | Arnett Gardens v Cavalier | W | 0-2 |
| Jamaica Premier League | 2014/10/12 22:00 | Cavalier v Harbour View FC | W | 1-0 |
| Jamaica Premier League | 2014/10/05 23:30 | Humble Lions v Cavalier | W | 0-1 |
| Jamaica Premier League | 2014/09/28 22:00 | Cavalier v Montego Bay Utd | W | 1-0 |
| Jamaica Premier League | 2014/09/21 20:30 | Barbican FC v Cavalier | D | 0-0 |