[1] Tivoli Gardens 1-0 Dunbeholden FC [10] 2018-09-30 20:30
Stadium: Edward Seaga Sports Complex Round: 3
Home History
| Jamajka - Premier League | 2018/09/23 20:30 | Tivoli Gardens v Reno FC | W | 2-1 |
| Jamajka - Premier League | 2018/09/16 20:30 | Montego Bay Utd v Tivoli Gardens | W | 0-2 |
| Puchar Jamajki | 2018/04/13 00:04 | Tivoli Gardens v Harbour View FC | W | 1-0 |
| Jamajka - Premier League | 2018/04/04 20:05 | Tivoli Gardens v Cavalier | L | 0-2 |
| Jamajka - Premier League | 2018/04/01 23:00 | Cavalier v Tivoli Gardens | D | 0-0 |
| Jamajka - Premier League | 2018/03/21 20:00 | UWI FC v Tivoli Gardens | L | 1-0 |
| Jamajka - Premier League | 2018/03/18 21:00 | Tivoli Gardens v Boys Town | W | 3-1 |
| Jamajka - Premier League | 2018/03/11 20:00 | Humble Lions v Tivoli Gardens | D | 1-1 |
Away History
| Jamajka - Premier League | 2018/09/23 20:30 | Dunbeholden FC v Montego Bay Utd | L | 0-1 |
| Jamajka - Premier League | 2018/09/18 01:35 | Waterhouse v Dunbeholden FC | L | 1-0 |
| Jamajka - Super League | 2018/06/06 21:01 | Barbican FC v Dunbeholden FC | D | 0-0 |