| 2026-10-17 15:40:48October 17, 2026 |   Signal Hill Secondary vs Hillview College | 15:40:483:40 pm | Premiership - Boys | 2026 | Signal Hill Secondary Gr. | Recap | Round 10 |
| 2026-10-17 15:40:47October 17, 2026 |   Trinity College East vs Naparima College | 15:40:473:40 pm | Premiership - Boys | 2026 | Trinity College East Gr. | Recap | Round 10 |
| 2026-10-17 15:40:37October 17, 2026 |   St. Benedict's College vs Fatima College | 15:40:373:40 pm | Premiership - Boys | 2026 | | Recap | Round 10 |
| 2026-10-17 15:40:22October 17, 2026 |  Mucurapo West Secondary vs St. Mary's College | 15:40:223:40 pm | Premiership - Boys | 2026 | Mucurapo West Secondary Gr. | Recap | Round 10 |
| 2026-10-17 15:40:09October 17, 2026 |   San Juan North Secondary vs St. Anthony's College | 15:40:093:40 pm | Premiership - Boys | 2026 | San Juan North Secondary School Gr. | Recap | Round 10 |
| 2026-10-17 15:40:06October 17, 2026 |   St. Augustine Secondary vs Presentation College | 15:40:063:40 pm | Premiership - Boys | 2026 | St. Augustine Secondary Gr. | Recap | Round 10 |
| 2026-10-17 15:40:06October 17, 2026 |   Queen's Royal College vs Malick Secondary | 15:40:063:40 pm | Premiership - Boys | 2026 | Queen’s Royal College Gr. | Recap | Round 10 |
| 2026-10-14 15:40:52October 14, 2026 | St. Mary's College vs Malick Secondary | 3 - 1 | Premiership - Boys | 2026 | St. Mary’s College Ground | Recap | Round 9 |
| 2026-10-14 15:40:51October 14, 2026 | San Juan North Secondary vs Mucurapo West Secondary | 4 - 1 | Premiership - Boys | 2026 | San Juan North Secondary School Gr. | Recap | Round 9 |
| 2026-10-14 15:40:47October 14, 2026 | Trinity College East vs St. Augustine Secondary | 3 - 3 | Premiership - Boys | 2026 | Trinity College East Gr. | Recap | Round 9 |
| 2026-10-14 15:40:44October 14, 2026 |  St. Anthony's College vs Arima North Secondary | 3 - 1 | Premiership - Boys | 2026 | St. Anthony’s College Gr. | Recap | Round 9 |
| 2026-10-14 15:40:35October 14, 2026 | Naparima College vs Hillview College | 2 - 1 | Premiership - Boys | 2026 | Lewis Street, San Fernando | Recap | Round 9 |
| 2026-10-14 15:40:24October 14, 2026 | Queen's Royal College vs Fatima College | 1 - 3 | Premiership - Boys | 2026 | Queen’s Royal College Gr. | Recap | Round 9 |
| 2026-10-14 15:40:24October 14, 2026 |  Presentation College vs Speyside Secondary | 3 - 0 | Premiership - Boys | 2026 | Mannie Ramjohn Stadium | Recap | Round 9 |
| 2026-10-14 15:40:18October 14, 2026 | St. Benedict's College vs Signal Hill Secondary | 2 - 1 | Premiership - Boys | 2026 | | Recap | Round 9 |
| 2026-10-10 15:40:54October 10, 2026 | Mucurapo West Secondary vs Malick Secondary | 3 - 5 | Premiership - Boys | 2026 | Mucurapo West Secondary Gr. | Recap | Round 8 |
| 2026-10-10 15:40:45October 10, 2026 | St. Benedict's College vs St. Augustine Secondary | 7 - 0 | Premiership - Boys | 2026 | | Recap | Round 8 |
| 2026-10-10 15:40:34October 10, 2026 | Hillview College vs Speyside Secondary | 1 - 3 | Premiership - Boys | 2026 | Hillview College Gr. | Recap | Round 8 |
| 2026-10-10 15:40:34October 10, 2026 |  Trinity College Moka vs Signal Hill Secondary | 15:40:343:40 pm | Premiership - Boys | 2026 | Trinity College Moka Gr. | Recap | Round 8 |
| 2026-10-10 15:40:33October 10, 2026 | Presentation College vs St. Mary's College | 2 - 2 | Premiership - Boys | 2026 | Mannie Ramjohn Stadium | Recap | Round 8 |
| 2026-10-10 15:40:18October 10, 2026 | St. Anthony's College vs Fatima College | 0 - 1 | Premiership - Boys | 2026 | St. Anthony’s College Gr. | Recap | Round 8 |
| 2026-10-10 15:40:18October 10, 2026 | Naparima College vs Arima North Secondary | 2 - 0 | Premiership - Boys | 2026 | Lewis Street, San Fernando | Recap | Round 8 |
| 2026-10-10 15:40:13October 10, 2026 | Queen's Royal College vs Trinity College East | 4 - 0 | Premiership - Boys | 2026 | Queen’s Royal College Gr. | Recap | Round 8 |
| 2026-10-07 15:40:54October 7, 2026 | St. Augustine Secondary vs Naparima College | 1 - 3 | Premiership - Boys | 2026 | St. Augustine Secondary Gr. | Recap | Round 7 |
| 2026-10-07 15:40:46October 7, 2026 | Presentation College vs Trinity College Moka | 5 - 0 | Premiership - Boys | 2026 | Mannie Ramjohn Stadium | Recap | Round 7 |
| 2026-10-07 15:40:40October 7, 2026 | Arima North Secondary vs Mucurapo West Secondary | 2 - 0 | Premiership - Boys | 2026 | Larry Gomes Stadium | Recap | Round 7 |
| 2026-10-07 15:40:35October 7, 2026 | Fatima College vs St. Mary's College | 1 - 1 | Premiership - Boys | 2026 | Fatima College Sports Gr. | Recap | Round 7 |
| 2026-10-07 15:40:22October 7, 2026 | Malick Secondary vs San Juan North Secondary | 1 - 3 | Premiership - Boys | 2026 | | Recap | Round 7 |
| 2026-10-07 15:40:14October 7, 2026 | St. Benedict's College vs Hillview College | 1 - 1 | Premiership - Boys | 2026 | | Recap | Round 7 |
| 2026-10-07 15:40:01October 7, 2026 | Speyside Secondary vs Trinity College East | 6 - 1 | Premiership - Boys | 2026 | Speyside Rec. Ground | Recap | Round 7 |
| 2026-10-07 15:40:01October 7, 2026 | Signal Hill Secondary vs Queen's Royal College | 2 - 1 | Premiership - Boys | 2026 | Signal Hill Secondary Gr. | Recap | Round 7 |
| 2026-10-03 15:40:57October 3, 2026 | Queen's Royal College vs St. Benedict's College | 1 - 1 | Premiership - Boys | 2026 | Queen’s Royal College Gr. | Recap | Round 6 |
| 2026-10-03 15:40:52October 3, 2026 | Arima North Secondary vs Fatima College | 0 - 5 | Premiership - Boys | 2026 | Arima Velodrome | Recap | Round 6 |
| 2026-10-03 15:40:48October 3, 2026 | Trinity College East vs St. Anthony's College | 2 - 2 | Premiership - Boys | 2026 | Trinity College East Gr. | Recap | Round 6 |
| 2026-10-03 15:40:44October 3, 2026 | St. Mary's College vs Hillview College | 1 - 1 | Premiership - Boys | 2026 | St. Mary’s College Ground | Recap | Round 6 |
| 2026-10-03 15:40:41October 3, 2026 | Signal Hill Secondary vs San Juan North Secondary | 2 - 1 | Premiership - Boys | 2026 | Signal Hill Secondary Gr. | Recap | Round 6 |
| 2026-10-03 15:40:24October 3, 2026 | St. Augustine Secondary vs Trinity College Moka | 5 - 2 | Premiership - Boys | 2026 | St. Augustine Secondary Gr. | Recap | Round 6 |
| 2026-10-03 15:40:21October 3, 2026 | Naparima College vs Speyside Secondary | 4 - 0 | Premiership - Boys | 2026 | Lewis Street, San Fernando | Recap | Round 6 |
| 2026-10-03 15:40:17October 3, 2026 | Mucurapo West Secondary vs Presentation College | 0 - 3 | Premiership - Boys | 2026 | Mucurapo West Secondary Gr. | Recap | Round 6 |
| 2026-09-30 15:40:59September 30, 2026 | Naparima College vs St. Mary's College | 1 - 2 | Premiership - Boys | 2026 | Lewis Street, San Fernando | Recap | Round 5 |
| 2026-09-30 15:40:53September 30, 2026 | Arima North Secondary vs St. Benedict's College | 0 - 4 | Premiership - Boys | 2026 | Arima Velodrome | Recap | Round 5 |
| 2026-09-30 15:40:51September 30, 2026 | Fatima College vs Trinity College East | 5 - 1 | Premiership - Boys | 2026 | Fatima College Sports Gr. | Recap | Round 5 |
| 2026-09-30 15:40:49September 30, 2026 | Signal Hill Secondary vs Presentation College | 3 - 2 | Premiership - Boys | 2026 | Signal Hill Secondary Gr. | Recap | Round 5 |
| 2026-09-30 15:40:46September 30, 2026 | Malick Secondary vs St. Augustine Secondary | 5 - 1 | Premiership - Boys | 2026 | | Recap | Round 5 |
| 2026-09-30 15:40:12September 30, 2026 | San Juan North Secondary vs Queen's Royal College | 1 - 2 | Premiership - Boys | 2026 | San Juan North Secondary School Gr. | Recap | Round 5 |
| 2026-09-30 15:40:11September 30, 2026 | Mucurapo West Secondary vs Speyside Secondary | 3 - 1 | Premiership - Boys | 2026 | Mucurapo West Secondary Gr. | Recap | Round 5 |
| 2026-09-30 15:40:03September 30, 2026 | Trinity College Moka vs St. Anthony's College | 1 - 1 | Premiership - Boys | 2026 | Trinity College Moka Gr. | Recap | Round 5 |
| 2026-09-26 15:40:34September 26, 2026 | Trinity College East vs Arima North Secondary | 2 - 3 | Premiership - Boys | 2026 | Trinity College East Gr. | Recap | Round 4 |
| 2026-09-26 15:40:32September 26, 2026 | St. Augustine Secondary vs San Juan North Secondary | 5 - 3 | Premiership - Boys | 2026 | St. Augustine Secondary Gr. | Recap | Round 4 |
| 2026-09-26 15:40:29September 26, 2026 | St. Anthony's College vs St. Benedict's College | 2 - 4 | Premiership - Boys | 2026 | St. Anthony’s College Gr. | Recap | Round 4 |
| 2026-09-26 15:40:22September 26, 2026 |  Speyside Secondary vs St. Mary's College | 2 - 7 | Premiership - Boys | 2026 | Speyside Rec. Ground | Recap | Round 4 |
| 2026-09-26 15:40:21September 26, 2026 | Malick Secondary vs Signal Hill Secondary | 0 - 4 | Premiership - Boys | 2026 | | Recap | Round 4 |
| 2026-09-26 15:40:16September 26, 2026 | Fatima College vs Naparima College | 2 - 2 | Premiership - Boys | 2026 | Fatima College Sports Gr. | Recap | Round 4 |
| 2026-09-26 15:40:14September 26, 2026 | Hillview College vs Mucurapo West Secondary | 4 - 1 | Premiership - Boys | 2026 | Hillview College Gr. | Recap | Round 4 |
| 2026-09-26 15:40:07September 26, 2026 | Trinity College Moka vs Queen's Royal College | 4 - 0 | Premiership - Boys | 2026 | Trinity College Moka Gr. | Recap | Round 4 |
| 2026-09-23 15:40:58September 23, 2026 | Malick Secondary vs St. Benedict's College | 0 - 1 | Premiership - Boys | 2026 | | Recap | Round 3 |
| 2026-09-23 15:40:50September 23, 2026 | St. Mary's College vs St. Anthony's College | 3 - 0 | Premiership - Boys | 2026 | St. Mary’s College Ground | Recap | Round 3 |
| 2026-09-23 15:40:40September 23, 2026 | Trinity College East vs Presentation College | 0 - 2 | Premiership - Boys | 2026 | Trinity College East Gr. | Recap | Round 3 |
| 2026-09-23 15:40:24September 23, 2026 | Fatima College vs Hillview College | 3 - 6 | Premiership - Boys | 2026 | Fatima College Sports Gr. | Recap | Round 3 |
| 2026-09-23 15:40:23September 23, 2026 | Signal Hill Secondary vs Naparima College | 2 - 1 | Premiership - Boys | 2026 | Signal Hill Secondary Gr. | Recap | Round 3 |
| 2026-09-23 15:40:18September 23, 2026 | Queen's Royal College vs Mucurapo West Secondary | 1 - 1 | Premiership - Boys | 2026 | Queen’s Royal College Gr. | Recap | Round 3 |
| 2026-09-23 15:40:15September 23, 2026 | Arima North Secondary vs Speyside Secondary | 8 - 0 | Premiership - Boys | 2026 | Larry Gomes Stadium | Recap | Round 3 |
| 2026-09-23 15:40:06September 23, 2026 | San Juan North Secondary vs Trinity College Moka | 1 - 4 | Premiership - Boys | 2026 | San Juan North Secondary School Gr. | Recap | Round 3 |
| 2026-09-19 15:40:59September 19, 2026 | Queen's Royal College vs St. Mary's College | 0 - 1 | Premiership - Boys | 2026 | | Recap | Round 2 |
| 2026-09-19 15:40:56September 19, 2026 | Malick Secondary vs Trinity College East | 6 - 2 | Premiership - Boys | 2026 | | Recap | Round 2 |
| 2026-09-19 15:40:53September 19, 2026 | Speyside Secondary vs St. Anthony's College | 15:40:533:40 pm | Premiership - Boys | 2026 | Speyside Rec. Ground | Recap | Round 2 |
| 2026-09-19 15:40:50September 19, 2026 | St. Benedict's College vs San Juan North Secondary | 15:40:503:40 pm | Premiership - Boys | 2026 | Ato Boldon Stadium | Recap | Round 2 |
| 2026-09-19 15:40:36September 19, 2026 | Mucurapo West Secondary vs St. Augustine Secondary | 2 - 2 | Premiership - Boys | 2026 | | Recap | Round 2 |
| 2026-09-19 15:40:30September 19, 2026 | Presentation College vs Fatima College | 2 - 2 | Premiership - Boys | 2026 | Mannie Ramjohn Stadium | Recap | Round 2 |
| 2026-09-19 15:40:24September 19, 2026 | Naparima College vs Trinity College | 7 - 0 | Premiership - Boys | 2026 | Lewis Street, San Fernando | Recap | - |
| 2026-09-19 15:40:02September 19, 2026 | Hillview College vs Arima North Secondary | 3 - 4 | Premiership - Boys | 2026 | Hillview College Gr. | Recap | Round 2 |
| 2026-09-16 20:11:29September 16, 2026 | Trinity College vs St. Benedict's College | 0 - 5 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-16 20:07:57September 16, 2026 | Trinity College East vs San Juan North Secondary | 2 - 1 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-16 19:46:54September 16, 2026 | St. Mary's College vs St. Augustine Secondary | 3 - 0 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-16 15:41:51September 16, 2026 | Presentation College San Fernando vs Arima North Secondary | 0 - 3 | Premiership - Boys | 2026 | Mannie Ramjohn Stadium | Recap | - |
| 2026-09-16 10:54:27September 16, 2026 | Signal Hill Secondary vs Mucurapo West Secondary | 3 - 0 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-16 09:36:29September 16, 2026 | Fatima College vs Malick Secondary | 4 - 1 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-16 09:32:48September 16, 2026 | Queen's Royal College vs Speyside Secondary | 0 - 0 | Premiership - Boys | 2026 | | Recap | Round 1 |
| 2026-09-11 17:00:04September 11, 2026 | Naparima College vs St. Benedict’s College | 6 - 0 | Premiership - Boys | 2026 | Ato Boldon Stadium | Recap | - |
