Head to Head
| Jamaica Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | W | 0-1 |
| Jamaica Premier League | 2019/11/17 20:00 | Tivoli Gardens v Portmore United | L | 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 | W | 3-2 |
| Jamaica Premier League | 2018/11/28 20:00 | Portmore United v Tivoli Gardens | L | 2-0 |
| Jamaica Premier League | 2018/11/04 20:00 | Portmore United v Tivoli Gardens | W | 0-1 |
| Jamaica Premier League | 2018/01/31 20:00 | Tivoli Gardens v Portmore United | L | 1-2 |
| Jamaica Premier League | 2017/12/21 20:00 | Portmore United v Tivoli Gardens | L | 2-0 |
Home History
| Jamaica Premier League | 2021/07/06 18:00 | Tivoli Gardens v Arnett Gardens | W | 1-0 |
| Jamaica Premier League | 2021/06/26 18:00 | Mount Pleasant FA v Tivoli Gardens | D | 0-0 |
| Jamaica Premier League | 2020/03/08 20:30 | Tivoli Gardens v Vere United | W | 5-1 |
| Jamaica Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | W | 0-1 |
| Jamaica Premier League | 2020/02/23 20:30 | Tivoli Gardens v Waterhouse | W | 4-3 |
| Jamaica Premier League | 2020/02/18 01:00 | Cavalier v Tivoli Gardens | D | 1-1 |
| Jamaica Premier League | 2020/01/30 20:00 | Tivoli Gardens v Mount Pleasant FA | L | 0-2 |
| Jamaica Premier League | 2020/01/27 01:00 | Arnett Gardens v Tivoli Gardens | D | 1-1 |
Away History
| Jamaica Premier League | 2021/07/10 18:00 | Portmore United v Molynes United FC | W | 1-0 |
| Jamaica Premier League | 2021/07/06 20:30 | Vere United v Portmore United | L | 1-0 |
| Jamaica Premier League | 2021/06/27 16:00 | Portmore United v Dunbeholden FC | W | 2-0 |
| Jamaica Premier League | 2020/03/08 20:30 | UWI FC v Portmore United | W | 1-3 |
| Jamaica Premier League | 2020/03/05 20:00 | Portmore United v Harbour View FC | D | 0-0 |
| Jamaica Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | L | 0-1 |
| CONCACAF Champions Cup | 2020/02/26 03:15 | Cruz Azul v Portmore United | L | 4-0 |
| CONCACAF Champions Cup | 2020/02/19 01:00 | Portmore United v Cruz Azul | L | 1-2 |