Head to Head
| Jamaica Premier League | 2025/03/19 20:30 | Dunbeholden FC v Tivoli Gardens | L | 2-4 |
| Jamaica Premier League | 2025/01/19 20:00 | Tivoli Gardens v Dunbeholden FC | L | 2-0 |
| Jamaica Premier League | 2024/11/21 20:00 | Dunbeholden FC v Tivoli Gardens | W | 2-1 |
| Jamaica Premier League | 2024/03/10 20:30 | Tivoli Gardens v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2023/12/10 20:30 | Dunbeholden FC v Tivoli Gardens | D | 2-2 |
| Jamaica Cup | 2023/04/20 23:00 | Dunbeholden FC v Tivoli Gardens | W | 6-3 |
| Jamaica Premier League | 2023/03/05 20:00 | Dunbeholden FC v Tivoli Gardens | W | 4-1 |
| Jamaica Premier League | 2022/12/04 22:00 | Tivoli Gardens v Dunbeholden FC | W | 0-2 |
Home History
| Jamaica Premier League | 2025/09/15 22:00 | Molynes United FC v Dunbeholden FC | W | 0-2 |
| Jamaica Premier League | 2025/09/07 20:00 | Dunbeholden FC v Montego Bay Utd | L | 1-2 |
| Jamaica Premier League | 2025/08/31 20:00 | Spanish Town Police v Dunbeholden FC | W | 0-1 |
| Jamaica Premier League | 2025/08/25 22:00 | Dunbeholden FC v Portmore United | L | 0-2 |
| Jamaica Premier League | 2025/05/04 20:30 | Waterhouse v Dunbeholden FC | L | 2-0 |
| Jamaica Premier League | 2025/04/27 20:30 | Dunbeholden FC v Portmore United | W | 1-0 |
| Jamaica Premier League | 2025/04/20 20:30 | Humble Lions v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2025/04/13 20:30 | Dunbeholden FC v Molynes United FC | L | 0-2 |
Away History
| Jamaica Premier League | 2025/09/15 00:00 | Montego Bay Utd v Tivoli Gardens | L | 3-1 |
| Jamaica Premier League | 2025/09/08 22:00 | Tivoli Gardens v Spanish Town Police | W | 2-1 |
| Jamaica Premier League | 2025/08/31 22:30 | Portmore United v Tivoli Gardens | D | 0-0 |
| Jamaica Premier League | 2025/08/24 20:00 | Chapelton Maroons FC v Tivoli Gardens | L | 2-1 |
| Jamaica Play-Offs | 2025/05/13 02:00 | Montego Bay Utd v Tivoli Gardens | D | 1-1 |
| Jamaica Play-Offs | 2025/05/09 23:00 | Tivoli Gardens v Montego Bay Utd | L | 1-2 |
| Jamaica Premier League | 2025/05/04 20:30 | Tivoli Gardens v Montego Bay Utd | W | 2-1 |
| Jamaica Premier League | 2025/04/27 20:30 | Chapelton Maroons FC v Tivoli Gardens | D | 2-2 |