| Premier League | 第39轮 | 2025-04-20 06:00 | Waterhouse | | Dunbeholden | |
| Premier League | 第38轮 | 2025-04-13 06:00 | Dunbeholden | | 波特莫尔联 | |
| Premier League | 第37轮 | 2025-04-06 06:00 | 胡曼伯狮子 | | Dunbeholden | |
| Premier League | 第36轮 | 2025-03-30 07:00 | Dunbeholden | | 莫利尼斯联 | |
| Premier League | 第35轮 | 2025-03-23 07:00 | Montego Bay United | | Dunbeholden | |
| Premier League | 第34轮 | 2025-03-16 07:00 | Dunbeholden | | Chapelton | |
| Premier League | 第33轮 | 2025-03-09 07:00 | Dunbeholden | | Harbour View | |
| Premier League | 第32轮 | 2025-03-05 07:00 | Jamalco | | Dunbeholden | |
| Premier League | 第31轮 | 2025-03-02 07:00 | Dunbeholden | | Tivoli Gardens | |
| Premier League | 第30轮 | 2025-02-26 07:00 | Cavalier | | Dunbeholden | |
| Premier League | 第29轮 | 2025-02-23 07:00 | Dunbeholden | | Mount Pleasant Academy | |
| Premier League | 第28轮 | 2025-02-19 07:00 | Racing United | | Dunbeholden | |
| Premier League | 第27轮 | 2025-02-16 07:00 | 阿内特加登斯 | | Dunbeholden | |
| Premier League | 第26轮 | 2025-02-09 07:00 | Dunbeholden | | Waterhouse | |
| Premier League | 第25轮 | 2025-02-05 07:00 | 波特莫尔联 | | Dunbeholden | |
| Premier League | 第24轮 | 2025-02-02 07:00 | Dunbeholden | | 胡曼伯狮子 | |
| Premier League | 第21轮 | 2025-01-30 05:30 | Chapelton | | Dunbeholden | 0-1 |
| Premier League | 第23轮 | 2025-01-29 07:00 | 莫利尼斯联 | | Dunbeholden | |
| Premier League | 第20轮 | 2025-01-27 04:00 | Harbour View | 4-1 | Dunbeholden | 3-0 |
| Premier League | 第22轮 | 2025-01-26 07:00 | Dunbeholden | | Montego Bay United | |
| Premier League | 第19轮 | 2025-01-23 04:00 | Dunbeholden | 1-4 | Jamalco | 0-0 |
| Premier League | 第18轮 | 2025-01-20 04:00 | Tivoli Gardens | 2-0 | Dunbeholden | 0-0 |
| Premier League | 第17轮 | 2025-01-13 04:00 | Dunbeholden | 0-2 | Cavalier | 0-0 |
| Premier League | 第16轮 | 2025-01-06 04:15 | Mount Pleasant Academy | 4-0 | Dunbeholden | 2-0 |
| Premier League | 第15轮 | 2024-12-30 04:00 | Dunbeholden | 2-2 | Racing United | 0-1 |
| Premier League | 第14轮 | 2024-12-23 04:00 | Dunbeholden | 0-1 | 阿内特加登斯 | 0-1 |
| Premier League | 第13轮 | 2024-12-09 04:00 | Waterhouse | 3-2 | Dunbeholden | 1-1 |
| Premier League | 第12轮 | 2024-12-02 04:00 | Dunbeholden | 3-3 | 波特莫尔联 | 0-1 |
| Premier League | 第11轮 | 2024-11-25 04:00 | 胡曼伯狮子 | 0-0 | Dunbeholden | 0-0 |
| Premier League | 第5轮 | 2024-11-22 04:00 | Dunbeholden | 2-1 | Tivoli Gardens | 1-1 |
| Premier League | 第10轮 | 2024-11-19 06:00 | Dunbeholden | | 莫利尼斯联 | |
| Premier League | 第9轮 | 2024-11-11 06:30 | Montego Bay United | 2-1 | Dunbeholden | 1-1 |
| Premier League | 第8轮 | 2024-11-04 04:00 | Dunbeholden | 2-0 | Chapelton | 1-0 |
| Premier League | 第3轮 | 2024-10-31 04:00 | Dunbeholden | 3-2 | Mount Pleasant Academy | 1-1 |
| Premier League | 第7轮 | 2024-10-28 04:00 | Dunbeholden | 1-0 | Harbour View | 1-0 |
| Premier League | 第6轮 | 2024-10-21 04:00 | Jamalco | 3-0 | Dunbeholden | 1-0 |
| Premier League | 第4轮 | 2024-10-08 04:00 | Cavalier | 4-1 | Dunbeholden | 2-1 |
| Premier League | 第2轮 | 2024-09-23 04:30 | Racing United | 1-0 | Dunbeholden | 1-0 |
| Premier League | 第1轮 | 2024-09-16 08:30 | 阿内特加登斯 | 3-0 | Dunbeholden | 2-0 |
| Premier League | - | 2024-04-08 04:30 | Dunbeholden | 4-2 | Jamalco | 2-0 |
| Premier League | - | 2024-04-01 04:30 | Dunbeholden | 2-4 | Cavalier | 1-1 |
| Premier League | - | 2024-03-25 05:00 | Waterhouse | 1-0 | Dunbeholden | 1-0 |
| Premier League | - | 2024-03-21 04:30 | Dunbeholden | 0-2 | Montego Bay United | 0-0 |
| Premier League | - | 2024-03-11 04:30 | Tivoli Gardens | 1-1 | Dunbeholden | 1-1 |
| Premier League | - | 2024-03-05 08:30 | Dunbeholden | 3-0 | Harbour View | 1-0 |
| Premier League | - | 2024-02-26 02:00 | 莫利尼斯联 | 2-4 | Dunbeholden | 2-1 |
| Premier League | - | 2024-02-19 02:00 | Lime Hall Academy | 1-4 | Dunbeholden | 0-1 |
| Premier League | - | 2024-02-12 04:30 | Dunbeholden | 1-1 | Treasure Beach | 1-1 |
| Premier League | - | 2024-02-05 04:00 | 波特莫尔联 | 1-1 | Dunbeholden | 0-1 |
| Premier League | - | 2024-01-29 04:00 | Dunbeholden | 1-2 | Mount Pleasant Academy | 0-2 |
| Premier League | - | 2024-01-22 04:00 | 胡曼伯狮子 | 0-0 | Dunbeholden | 0-0 |
| Premier League | - | 2024-01-16 08:30 | Dunbeholden | 0-1 | 阿内特加登斯 | 0-0 |
| Premier League | - | 2024-01-11 07:00 | Harbour View | | Dunbeholden | |
| Premier League | - | 2024-01-04 04:00 | Jamalco | 1-2 | Dunbeholden | 0-0 |
| Premier League | - | 2024-01-01 06:15 | Cavalier | | Dunbeholden | |
| Premier League | - | 2023-12-28 04:00 | Dunbeholden | 2-1 | Waterhouse | 0-1 |
| Premier League | - | 2023-12-22 04:00 | Dunbeholden | 1-0 | 胡曼伯狮子 | 1-0 |
| Premier League | - | 2023-12-18 04:00 | Montego Bay United | 1-2 | Dunbeholden | 1-0 |
| Premier League | - | 2023-12-11 04:30 | Dunbeholden | 2-2 | Tivoli Gardens | 2-1 |
| Premier League | - | 2023-11-27 07:00 | Dunbeholden | | 莫利尼斯联 | 1-0 |
| Premier League | - | 2023-11-23 04:00 | Dunbeholden | 2-1 | Lime Hall Academy | 2-1 |
| Premier League | - | 2023-11-20 04:00 | Treasure Beach | 0-0 | Dunbeholden | 0-0 |
| Premier League | - | 2023-11-13 04:00 | Dunbeholden | 0-2 | 波特莫尔联 | 0-1 |
| Premier League | - | 2023-11-06 04:15 | Mount Pleasant Academy | 0-0 | Dunbeholden | |
| Premier League | 第1轮 | 2023-10-24 08:30 | 阿内特加登斯 | 0-0 | Dunbeholden | 0-0 |
| Concacaf Caribbean Club Championship | 第4轮 | 2023-09-29 08:00 | Dunbeholden | 2-1 | Cibao | 1-0 |
| Concacaf Caribbean Club Championship | 第3轮 | 2023-09-22 08:00 | Dunbeholden | 0-2 | Robin Hood | 0-1 |
| Concacaf Caribbean Club Championship | 第2轮 | 2023-08-31 08:00 | Deportivo Pantoja | 1-1 | Dunbeholden | 1-0 |
| Concacaf Caribbean Club Championship | 第1轮 | 2023-08-24 06:06 | Harbour View | 1-0 | Dunbeholden | 0-0 |
| Premier League | - | 2023-05-23 09:00 | Mount Pleasant Academy | 3-0 | Dunbeholden | 0-0 |
| Premier League | - | 2023-05-16 06:00 | Dunbeholden | | Mount Pleasant Academy | |
| Premier League | - | 2023-05-08 04:15 | Dunbeholden | 3-1 | Mount Pleasant Academy | |
| Premier League | - | 2023-05-01 06:30 | Chapelton | | Dunbeholden | |
| Premier League | - | 2023-04-25 06:00 | Dunbeholden | | Jamalco | |
| Premier League | - | 2023-04-18 06:00 | 阿内特加登斯 | | Dunbeholden | |
| Premier League | - | 2023-04-10 02:00 | Dunbeholden | | Montego Bay United | |
| Premier League | - | 2023-04-03 04:00 | 莫利尼斯联 | 2-3 | Dunbeholden | 0-2 |
| Premier League | - | 2023-03-28 08:30 | Waterhouse | 0-0 | Dunbeholden | 0-0 |
| Premier League | - | 2023-03-20 06:30 | Dunbeholden | | 波特莫尔联 | |
| Premier League | - | 2023-03-13 04:00 | Cavalier | 3-1 | Dunbeholden | 2-1 |
| Premier League | - | 2023-03-06 04:00 | Dunbeholden | 4-1 | Tivoli Gardens | 1-1 |
| Premier League | - | 2023-02-28 06:00 | Harbour View | | Dunbeholden | |
| Premier League | - | 2023-02-20 02:00 | Dunbeholden | 4-2 | Faulkland | 2-0 |
| Premier League | - | 2023-02-14 08:30 | Dunbeholden | 1-2 | 胡曼伯狮子 | 0-1 |
| Premier League | - | 2023-02-06 04:00 | Mount Pleasant Academy | 3-0 | Dunbeholden | 1-0 |
| Premier League | - | 2023-01-30 02:00 | Dunbeholden | 0-0 | Chapelton | 0-0 |
| Premier League | - | 2023-01-24 06:00 | Jamalco | | Dunbeholden | |
| Premier League | - | 2023-01-16 06:30 | Dunbeholden | | 阿内特加登斯 | |
| Premier League | - | 2023-01-09 04:15 | Montego Bay United | 0-2 | Dunbeholden | |
| Premier League | - | 2023-01-03 06:00 | Dunbeholden | | 莫利尼斯联 | |
| Premier League | - | 2022-12-29 02:00 | Dunbeholden | 0-0 | Waterhouse | 0-0 |
| Premier League | - | 2022-12-22 06:15 | 波特莫尔联 | 0-0 | Dunbeholden | 0-0 |
| Premier League | - | 2022-12-05 06:00 | Tivoli Gardens | | Dunbeholden | |
| Premier League | - | 2022-11-21 06:30 | Dunbeholden | | Cavalier | |
| Premier League | - | 2022-11-07 04:00 | Dunbeholden | 1-4 | Harbour View | 1-2 |
| Premier League | - | 2022-10-31 02:00 | Faulkland | 0-2 | Dunbeholden | 0-1 |
| Premier League | 第1轮 | 2022-10-24 04:00 | 胡曼伯狮子 | 0-0 | Dunbeholden | 0-0 |
| Premier League | - | 2022-07-04 07:00 | Dunbeholden | | Harbour View | 1-0 |
| Premier League | - | 2022-06-30 08:30 | Dunbeholden | 2-3 | Cavalier | |
| Premier League | - | 2022-06-27 04:00 | Cavalier | 0-1 | Dunbeholden | 0-1 |
| Premier League | 第22轮 | 2022-06-13 04:00 | Dunbeholden | 1-1 | Harbour View | |
| Premier League | 第19轮 | 2022-06-10 06:00 | Dunbeholden | | Cavalier | |
| Premier League | 第21轮 | 2022-06-06 04:00 | 胡曼伯狮子 | 3-1 | Dunbeholden | 2-0 |
| Premier League | 第20轮 | 2022-05-30 04:00 | Dunbeholden | 1-0 | 波特莫尔联 | 0-0 |
| Premier League | 第18轮 | 2022-05-16 04:00 | 阿内特加登斯 | 1-0 | Dunbeholden | 1-0 |
| Premier League | 第17轮 | 2022-05-09 04:00 | Dunbeholden | 1-1 | Tivoli Gardens | 1-0 |
| Premier League | 第16轮 | 2022-05-02 04:00 | Mount Pleasant Academy | 1-3 | Dunbeholden | 1-2 |
| Premier League | 第15轮 | 2022-04-26 06:00 | Dunbeholden | | 莫利尼斯联 | |
| Premier League | 第14轮 | 2022-04-18 06:15 | Dunbeholden | | Waterhouse | |
| Premier League | 第13轮 | 2022-04-11 04:00 | Montego Bay United | 0-1 | Dunbeholden | |
| Premier League | 第12轮 | 2022-04-05 08:30 | Dunbeholden | 1-0 | Jamalco | 1-0 |
| Premier League | 第11轮 | 2022-03-28 01:45 | Harbour View | 0-1 | Dunbeholden | 0-0 |
| Premier League | 第10轮 | 2022-03-22 04:00 | Dunbeholden | 1-0 | 胡曼伯狮子 | 0-0 |
| Premier League | 第9轮 | 2022-03-15 06:15 | 波特莫尔联 | 2-3 | Dunbeholden | 1-2 |
| Premier League | 第8轮 | 2022-03-08 02:00 | Cavalier | 1-2 | Dunbeholden | 0-2 |
| Premier League | 第7轮 | 2022-03-01 02:00 | Dunbeholden | 1-2 | 阿内特加登斯 | 0-0 |
| Premier League | 第6轮 | 2022-02-22 04:15 | Tivoli Gardens | 0-1 | Dunbeholden | 0-0 |
| Premier League | 第5轮 | 2022-02-14 02:00 | Dunbeholden | 1-1 | Mount Pleasant Academy | 0-0 |
| Premier League | 第4轮 | 2022-02-08 02:00 | 莫利尼斯联 | 0-1 | Dunbeholden | 0-0 |
| Premier League | 第3轮 | 2022-01-31 02:00 | Waterhouse | 4-1 | Dunbeholden | 1-0 |
| Premier League | 第2轮 | 2022-01-25 04:15 | Dunbeholden | 3-0 | Montego Bay United | 2-0 |
| Premier League | 第1轮 | 2022-01-18 02:00 | Jamalco | 1-2 | Dunbeholden | 0-1 |
| Premier League | 第11轮 | 2021-09-11 02:00 | Dunbeholden | 2-5 | Mount Pleasant Academy | 2-3 |
| Premier League | 第10轮 | 2021-09-05 01:00 | 阿内特加登斯 | 1-1 | Dunbeholden | 0-0 |
| Premier League | 第9轮 | 2021-08-28 02:00 | Dunbeholden | 2-1 | 胡曼伯狮子 | |
| Premier League | 第8轮 | 2021-08-17 04:30 | Tivoli Gardens | 1-1 | Dunbeholden | 1-1 |
| Premier League | 第7轮 | 2021-08-08 02:00 | Dunbeholden | | 西印度群岛大学 | |
| Premier League | 第6轮 | 2021-08-01 21:30 | Dunbeholden | 2-1 | Jamalco | 0-1 |
| Premier League | 第5轮 | 2021-07-25 04:30 | Dunbeholden | 3-1 | 莫利尼斯联 | 2-0 |
| Premier League | 第4轮 | 2021-07-18 04:30 | Harbour View | 2-0 | Dunbeholden | 2-0 |
| Premier League | 第3轮 | 2021-07-12 02:00 | Cavalier | 0-1 | Dunbeholden | 0-1 |
| Premier League | 第2轮 | 2021-07-04 04:30 | Dunbeholden | 0-2 | Waterhouse | 0-0 |
| Premier League | 第1轮 | 2021-06-28 00:00 | 波特莫尔联 | 2-0 | Dunbeholden | 1-0 |
| Premier League | 第33轮 | 2020-03-30 04:30 | Mount Pleasant Academy | | Dunbeholden | |
| Premier League | 第32轮 | 2020-03-26 05:30 | Dunbeholden | | 阿内特加登斯 | |
| Premier League | 第31轮 | 2020-03-23 04:30 | 西印度群岛大学 | | Dunbeholden | |
| Premier League | 第30轮 | 2020-03-16 04:30 | Dunbeholden | | Tivoli Gardens | |
| Premier League | 第29轮 | 2020-03-09 06:00 | 胡曼伯狮子 | 0-0 | Dunbeholden | 0-0 |
| Premier League | 第28轮 | 2020-03-02 04:30 | Dunbeholden | 2-0 | Harbour View | 1-0 |
| Premier League | 第27轮 | 2020-02-24 04:30 | 莫利尼斯联 | 2-4 | Dunbeholden | 2-2 |
| Premier League | 第26轮 | 2020-02-17 04:00 | Jamalco | 1-1 | Dunbeholden | 1-0 |
| Premier League | 第25轮 | 2020-01-31 04:00 | Dunbeholden | 1-4 | 波特莫尔联 | 0-2 |
| Premier League | 第24轮 | 2020-01-25 09:00 | Waterhouse | 3-1 | Dunbeholden | 2-1 |
| Premier League | 第23轮 | 2020-01-20 04:00 | Dunbeholden | 1-0 | Cavalier | 0-0 |
| Premier League | 第22轮 | 2020-01-13 04:00 | 西印度群岛大学 | 0-0 | Dunbeholden | 0-0 |
| Premier League | 第21轮 | 2020-01-06 04:00 | Dunbeholden | 2-0 | Cavalier | 1-0 |
| Premier League | 第20轮 | 2019-12-30 04:00 | 莫利尼斯联 | 2-3 | Dunbeholden | 1-2 |
| Premier League | 第19轮 | 2019-12-23 09:00 | 阿内特加登斯 | 0-3 | Dunbeholden | 0-3 |
| Premier League | 第18轮 | 2019-12-16 04:00 | Dunbeholden | 1-1 | Waterhouse | 0-0 |
| Premier League | 第17轮 | 2019-12-13 08:00 | Mount Pleasant Academy | 2-1 | Dunbeholden | 1-0 |
| Premier League | 第16轮 | 2019-12-09 04:00 | Dunbeholden | 0-1 | Tivoli Gardens | 0-0 |
| Premier League | 第15轮 | 2019-12-02 04:00 | 波特莫尔联 | 1-2 | Dunbeholden | 0-2 |
| Premier League | 第14轮 | 2019-11-28 04:00 | Dunbeholden | 1-1 | 胡曼伯狮子 | 0-0 |
| Premier League | 第13轮 | 2019-11-25 08:00 | Harbour View | 1-2 | Dunbeholden | 0-1 |
| Premier League | 第12轮 | 2019-11-18 04:00 | Dunbeholden | 2-1 | Jamalco | 1-1 |
| Premier League | 第11轮 | 2019-11-11 04:00 | Dunbeholden | 0-1 | Mount Pleasant Academy | 0-1 |
| Premier League | 第10轮 | 2019-11-05 09:00 | 阿内特加登斯 | 2-2 | Dunbeholden | 0-0 |
| Premier League | 第9轮 | 2019-10-28 04:30 | Dunbeholden | 1-0 | 西印度群岛大学 | 0-0 |
| Premier League | 第8轮 | 2019-10-21 04:30 | Tivoli Gardens | 1-0 | Dunbeholden | 0-0 |
| Premier League | 第7轮 | 2019-10-14 04:30 | Dunbeholden | 0-0 | 胡曼伯狮子 | 0-0 |
| Premier League | 第6轮 | 2019-10-08 09:30 | Harbour View | 1-0 | Dunbeholden | 0-0 |
| Premier League | 第5轮 | 2019-09-30 04:30 | Dunbeholden | 0-1 | 莫利尼斯联 | 0-1 |
| Premier League | 第4轮 | 2019-09-23 04:30 | Dunbeholden | 2-0 | Jamalco | 1-0 |
| Premier League | 第3轮 | 2019-09-16 04:30 | 波特莫尔联 | 0-1 | Dunbeholden | 0-1 |
| Premier League | 第2轮 | 2019-09-09 04:30 | Dunbeholden | 0-1 | Waterhouse | 0-1 |
| Premier League | 第1轮 | 2019-09-02 06:00 | Cavalier | 3-1 | Dunbeholden | 1-0 |
