[1] Portmore United 1-1 Tivoli Gardens [10] 2017-10-08 20:30
Stadium: Ferdi Neita Sports Complex Round: 3
Head to Head
| Jamaica Premier League | 2017/04/30 20:00 | Portmore United v Tivoli Gardens | W | 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 | L | 2-1 |
| Jamaica Premier League | 2016/12/21 20:00 | Portmore United v Tivoli Gardens | W | 2-0 |
| Jamaica Premier League | 2016/09/18 20:30 | Portmore United v Tivoli Gardens | L | 0-1 |
| Jamaica Premier League | 2016/02/28 20:00 | Tivoli Gardens v Portmore United | L | 1-0 |
| Jamaica Premier League | 2016/01/14 20:00 | Portmore United v Tivoli Gardens | W | 1-0 |
| Jamaica Premier League | 2015/11/04 20:00 | Tivoli Gardens v Portmore United | W | 1-2 |
Home History
| Jamaica Premier League | 2017/10/01 20:30 | Sandals South Coast FC v Portmore United | W | 0-4 |
| Jamaica Premier League | 2017/09/25 22:45 | Portmore United v Cavalier | W | 1-0 |
| CONCACAF League | 2017/08/10 00:00 | Plaza Amador v Portmore United | L | 6-4 |
| CONCACAF League | 2017/08/03 00:00 | Portmore United v Plaza Amador | W | 1-0 |
| Jamaica Play-Offs | 2017/06/06 01:30 | Arnett Gardens v Portmore United | L | 2-1 |
| Jamaica Premier League | 2017/05/28 20:00 | UWI FC v Portmore United | W | 0-2 |
| CFU Club Championship | 2017/05/18 21:36 | San Juan Jabloteh v Portmore United | D | 2-2 |
| CFU Club Championship | 2017/05/16 21:36 | Portmore United v Racing FC des Gonaives | W | 1-0 |
Away History
| Jamaica Premier League | 2017/10/01 23:00 | Tivoli Gardens v Arnett Gardens | L | 0-1 |
| Jamaica Premier League | 2017/09/24 20:30 | Reno FC v Tivoli Gardens | L | 1-0 |
| 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 | 2017/04/16 20:30 | Humble Lions v Tivoli Gardens | L | 4-0 |
| Jamaica Premier League | 2017/04/12 20:30 | Tivoli Gardens v Arnett Gardens | W | 3-0 |
| Jamaica Cup | 2017/04/10 02:39 | Barbican FC v Tivoli Gardens | W | 0-2 |
| Jamaica Premier League | 2017/04/02 20:10 | Reno FC v Tivoli Gardens | L | 1-0 |