[12] Boys Town 0-4 Portmore United [2] 2017-12-17 20:00
Weather: Hot Stadium: Collie Smith Drive Sporting Complex Pitch: Uneven and|cutting up Round: 16
Head to Head
| Jamaica Premier League | 2017/11/08 20:00 | Boys Town v Portmore United | L | 1-4 |
| Jamaica Premier League | 2017/03/07 01:00 | Portmore United v Boys Town | L | 4-0 |
| Jamaica Premier League | 2016/12/11 20:00 | Boys Town v Portmore United | D | 0-0 |
| Jamaica Premier League | 2016/09/25 20:30 | Boys Town v Portmore United | L | 1-2 |
| Jamaica Premier League | 2016/01/31 20:00 | Portmore United v Boys Town | W | 1-3 |
| Jamaica Premier League | 2015/12/13 20:00 | Portmore United v Boys Town | W | 0-3 |
| Jamaica Premier League | 2015/10/11 20:30 | Boys Town v Portmore United | D | 0-0 |
Home History
| Jamaica Premier League | 2017/12/13 20:00 | Tivoli Gardens v Boys Town | L | 3-0 |
| Jamaica Premier League | 2017/12/10 20:00 | Boys Town v UWI FC | L | 1-2 |
| Jamaica Premier League | 2017/12/03 20:00 | Boys Town v Waterhouse | L | 1-2 |
| Jamaica Premier League | 2017/11/26 20:00 | Sandals South Coast FC v Boys Town | L | 1-0 |
| Jamaica Premier League | 2017/11/23 00:30 | Waterhouse v Boys Town | D | 1-1 |
| Jamaica Premier League | 2017/11/19 20:00 | Boys Town v Tivoli Gardens | L | 2-4 |
| Jamaica Premier League | 2017/11/12 20:00 | Sandals South Coast FC v Boys Town | L | 1-0 |
| Jamaica Premier League | 2017/11/08 20:00 | Boys Town v Portmore United | L | 1-4 |
Away History
| Jamaica Premier League | 2017/12/13 20:00 | Portmore United v Waterhouse | W | 2-1 |
| Jamaica Premier League | 2017/12/10 20:00 | Sandals South Coast FC v Portmore United | W | 0-2 |
| Jamaica Premier League | 2017/12/03 20:00 | Portmore United v Montego Bay Utd | W | 5-1 |
| Jamaica Premier League | 2017/11/28 01:35 | Cavalier v Portmore United | D | 0-0 |
| Jamaica Premier League | 2017/11/24 00:00 | Harbour View FC v Portmore United | W | 0-1 |
| Jamaica Premier League | 2017/11/19 20:00 | Portmore United v Montego Bay Utd | D | 0-0 |
| Jamaica Premier League | 2017/11/12 20:00 | Portmore United v Arnett Gardens | D | 0-0 |
| Jamaica Premier League | 2017/11/08 20:00 | Boys Town v Portmore United | W | 1-4 |