[3] Tivoli Gardens 1-1 Portmore United [3] 2022-01-17 20:15
Stadium: Edward Seaga Sports Complex Round: 1
Head to Head
| Jamaica Premier League | 2021/07/19 20:30 | Tivoli Gardens v Portmore United | L | 1-3 |
| 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 |
| Jamaica Premier League | 2017/10/08 20:30 | Portmore United v Tivoli Gardens | D | 1-1 |
| Jamaica Premier League | 2017/04/30 20:00 | Portmore United v Tivoli Gardens | L | 2-1 |
| Jamaica Premier League | 2017/04/23 20:00 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2017/03/01 20:30 | Tivoli Gardens v Portmore United | W | 2-1 |
| Jamaica Premier League | 2016/12/21 20:00 | Portmore United v Tivoli Gardens | L | 2-0 |
| Jamaica Premier League | 2016/09/18 20:30 | Portmore United v Tivoli Gardens | W | 0-1 |
| Jamaica Premier League | 2016/02/28 20:00 | Tivoli Gardens v Portmore United | W | 1-0 |
| Jamaica Premier League | 2016/01/14 20:00 | Portmore United v Tivoli Gardens | L | 1-0 |
| Jamaica Premier League | 2015/11/04 20:00 | Tivoli Gardens v Portmore United | L | 1-2 |