Head to Head
| Jamaica Premier League | 2024/03/03 20:30 | Portmore United v Montego Bay Utd | D | 1-1 |
| Jamaica Premier League | 2023/12/03 20:00 | Montego Bay Utd v Portmore United | W | 3-2 |
| Jamaica Premier League | 2023/02/12 20:15 | Montego Bay Utd v Portmore United | D | 1-1 |
| Jamaica Premier League | 2022/10/23 18:00 | Portmore United v Montego Bay Utd | D | 1-1 |
| Jamaica Premier League | 2022/05/23 22:00 | Portmore United v Montego Bay Utd | W | 0-1 |
| Jamaica Premier League | 2022/03/07 20:15 | Montego Bay Utd v Portmore United | L | 0-1 |
| Jamaica Premier League | 2019/03/17 20:30 | Montego Bay Utd v Portmore United | L | 1-5 |
| Jamaica Premier League | 2019/01/16 20:00 | Portmore United v Montego Bay Utd | L | 1-0 |
| Jamaica Premier League | 2018/11/11 20:00 | Portmore United v Montego Bay Utd | L | 1-0 |
| Jamaica Premier League | 2018/03/18 21:00 | Montego Bay Utd v Portmore United | L | 1-2 |
| Jamaica Premier League | 2017/12/03 20:00 | Portmore United v Montego Bay Utd | L | 5-1 |
| Jamaica Premier League | 2017/11/19 20:00 | Portmore United v Montego Bay Utd | D | 0-0 |
| Jamaica Premier League | 2017/04/04 01:00 | Montego Bay Utd v Portmore United | D | 0-0 |
| Jamaica Premier League | 2017/01/15 20:00 | Portmore United v Montego Bay Utd | D | 1-1 |
| Jamaica Premier League | 2016/10/30 20:00 | Portmore United v Montego Bay Utd | L | 1-0 |
| Jamaica Premier League | 2016/05/01 21:00 | Portmore United v Montego Bay Utd | W | 1-2 |
| Jamaica Premier League | 2016/03/22 01:30 | Montego Bay Utd v Portmore United | L | 1-3 |
| Jamaica Premier League | 2015/11/15 20:00 | Portmore United v Montego Bay Utd | L | 1-0 |
| Jamaica Premier League | 2015/09/06 21:00 | Montego Bay Utd v Portmore United | L | 0-2 |