Head to Head
| Jamaica Premier League | 2023/01/08 20:00 | Tivoli Gardens v Portmore United | D | 0-0 |
| Jamaica Premier League | 2022/04/04 22:00 | Portmore United v Tivoli Gardens | D | 1-1 |
| Jamaica Premier League | 2022/01/17 20:15 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2021/07/19 20:30 | Tivoli Gardens v Portmore United | W | 1-3 |
| Jamaica Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | L | 0-1 |
| Jamaica Premier League | 2019/11/17 20:00 | Tivoli Gardens v Portmore United | W | 0-1 |
| Jamaica Premier League | 2019/10/06 20:30 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2019/03/11 00:00 | Tivoli Gardens v Portmore United | L | 3-2 |
Home History
| Jamaica Premier League | 2023/04/06 21:00 | Portmore United v Mount Pleasant FA | D | 0-0 |
| Jamaica Premier League | 2023/04/02 22:30 | Harbour View FC v Portmore United | W | 0-1 |
| Jamaica Premier League | 2023/03/26 21:00 | Portmore United v Faulkland FC | W | 4-0 |
| Jamaica Premier League | 2023/03/19 22:30 | Dunbeholden FC v Portmore United | W | 1-3 |
| Jamaica Premier League | 2023/03/06 22:00 | Portmore United v Chapelton Maroons FC | D | 0-0 |
| Jamaica Premier League | 2023/02/26 20:00 | Vere United v Portmore United | W | 0-2 |
| Jamaica Premier League | 2023/02/19 20:00 | Portmore United v Arnett Gardens | L | 1-2 |
| Jamaica Premier League | 2023/02/12 20:15 | Montego Bay Utd v Portmore United | D | 1-1 |
Away History
| Jamaica Premier League | 2023/04/02 20:00 | Tivoli Gardens v Cavalier | L | 0-1 |
| Jamaica Premier League | 2023/03/27 22:00 | Tivoli Gardens v Humble Lions | L | 1-2 |
| Jamaica Premier League | 2023/03/19 20:00 | Harbour View FC v Tivoli Gardens | D | 2-2 |
| Jamaica Premier League | 2023/03/12 20:00 | Tivoli Gardens v Faulkland FC | D | 0-0 |
| Jamaica Premier League | 2023/03/05 20:00 | Dunbeholden FC v Tivoli Gardens | L | 4-1 |
| Jamaica Premier League | 2023/02/26 20:00 | Tivoli Gardens v Mount Pleasant FA | L | 0-2 |
| Jamaica Premier League | 2023/02/20 22:00 | Chapelton Maroons FC v Tivoli Gardens | L | 2-0 |
| Jamaica Premier League | 2023/02/13 22:00 | Tivoli Gardens v Vere United | D | 0-0 |