Home History
| 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 |
Away History
| Jamaica Premier League | 2014/11/09 23:00 | Waterhouse v Boys Town | D | 0-0 |
| 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 Champions Cup | 2014/09/17 00:00 | Waterhouse v DC United | L | 1-2 |