| 2023-11-03 15:45:00November 3, 2023 |   Arima North Secondary | 0 - 2 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   Trinity College East vs Speyside Secondary | 3 - 1 | Premiership | 2023 | Trinity College East | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   St. Benedict’s College vs Malick Secondary School | 4 - 0 | Premiership | 2023 | Mahaica Sporting Complex | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   St. Mary’s College vs Fatima College | 0 - 1 | Premiership | 2023 | St. Mary's College | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   Naparima Boys College vs St. Anthony’s College | 1 - 2 | Premiership | 2023 | St. Anthony’s College | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   Presentation College vs East Mucurapo Secondary | 5 - 2 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-11-03 03:45:00November 3, 2023 |   Chaguanas North Secondary vs San Juan North Secondary | 0 - 2 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-31 03:30:00October 31, 2023 | Speyside Secondary | 2 | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-10-31 03:30:00October 31, 2023 |  Bishop's High School vs Trinity College East | 2 - 2 | Premiership | 2023 | Plymouth Rec. Ground | Recap |
| 2023-10-28 15:45:00October 28, 2023 |  Presentation College vs Pleasantville Secondary | 4 - 0 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-28 15:45:00October 28, 2023 | St. Mary’s College vs Chaguanas North Secondary | 3 - 1 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-10-28 15:45:00October 28, 2023 | Trinity College East vs St. Benedict's College | 0 - 5 | Premiership | 2023 | Trinity College East | Recap |
| 2023-10-28 15:30:00October 28, 2023 | Naparima College vs Fatima College | 1 - 2 | Premiership | 2023 | Lewis Street | Recap |
| 2023-10-28 03:45:00October 28, 2023 | East Mucurapo Secondary vs San Juan North Secondary | 2 - 2 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-10-28 03:45:00October 28, 2023 | Arima North Secondary vs St. Anthony's College | 1 - 1 | Premiership | 2023 | Larry Gomes Stadium | Recap |
| 2023-10-25 15:45:46October 25, 2023 | San Juan North Secondary vs St. Mary's College | 4 - 1 | Premiership | 2023 | San Juan North Secondary School | Recap |
| 2023-10-25 15:45:43October 25, 2023 | Pleasantville vs St. Benedict's College | 0 - 8 | Premiership | 2023 | Manny Ramjohn T. Field | Recap |
| 2023-10-25 15:45:30October 25, 2023 | Malick Secondary vs East Mucurapo Secondary | 5 - 0 | Premiership | 2023 | St Mary's College Grounds | Recap |
| 2023-10-25 15:45:07October 25, 2023 | Fatima College vs Trinity College East | 4 - 0 | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-10-25 15:30:56October 25, 2023 | Arima North Secondary vs Bishop's High School | 4 - 0 | Premiership | 2023 | | Recap |
| 2023-10-25 15:30:47October 25, 2023 | Chaguanas North Secondary vs Speyside Secondary | 1 - 1 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-25 15:30:14October 25, 2023 | Queen's Royal College vs Naparima College | 1 - 4 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-10-25 15:30:13October 25, 2023 | Presentation College vs St. Anthony's College | 1 - 0 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-25 03:45:00October 25, 2023 | Malick Secondary School vs East Mucurapo Secondary | 5 - 1 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-10-25 03:45:00October 25, 2023 | Fatima College vs Trinity College East | 4 - 0 | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-10-25 03:45:00October 25, 2023 | Naparima Boys College vs Queen's Royal College | 4 - 1 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-10-25 03:30:00October 25, 2023 | Arima North Secondary vs Bishops High School | 4 - 0 | Premiership | 2023 | Larry Gomes Stadium | Recap |
| 2023-10-25 03:30:00October 25, 2023 | Chaguanas North Secondary vs Speyside Secondary | 1 - 1 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-21 03:45:00October 21, 2023 | St. Benedict’s College vs Queen's Royal College | 4 - 2 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-21 03:45:00October 21, 2023 | St. Mary’s college vs Presentation College | 0 - 0 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-10-21 03:45:00October 21, 2023 | St. Anthony’s College vs Trinity College East | 2 - 4 | Premiership | 2023 | St. Anthony’s College | Recap |
| 2023-10-21 03:45:00October 21, 2023 |  San Juan North Sec vs Malick Secondary | 1 - 1 | Premiership | 2023 | San Juan North Sec. | Recap |
| 2023-10-21 03:45:00October 21, 2023 | Chaguanas North vs Arima North Sec. | 0 - 1 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-21 03:45:00October 21, 2023 | Fatima College vs Bishops High School | 3 - 0 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-10-21 03:30:00October 21, 2023 | Speyside High School vs Naparima College | 2 - 2 | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-10-21 03:30:00October 21, 2023 | East Mucurapo Sec. vs Pleasantville Sec. | 8 - 5 | Premiership | 2023 | Trinity College Moka | Recap |
| 2023-10-18 16:00:57October 18, 2023 | Malick Secondary vs Fatima College | 16:00:574:00 pm | Premiership | 2023 | St Mary's College Grounds | Recap |
| 2023-10-18 16:00:56October 18, 2023 | Trinity College East vs Chaguanas North Secondary | 16:00:564:00 pm | Premiership | 2023 | Trinity College East | Recap |
| 2023-10-18 16:00:37October 18, 2023 | St. Anthony's College vs San Juan North Secondary | 16:00:374:00 pm | Premiership | 2023 | St. Anthony’s College | Recap |
| 2023-10-18 16:00:32October 18, 2023 | Queen's Royal College vs Pleasantville Secondary | 16:00:324:00 pm | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-10-18 16:00:21October 18, 2023 | Naparima College vs Presentation College | 16:00:214:00 pm | Premiership | 2023 | Lewis Street | Recap |
| 2023-10-18 16:00:01October 18, 2023 | St. Benedict's College vs St. Mary's College | 5 - 0 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-18 15:30:51October 18, 2023 | East Mucurapo Secondary vs Bishop's High School | 15:30:513:30 pm | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-10-18 15:30:47October 18, 2023 | Speyside Secondary vs Arima North Secondary | 15:30:473:30 pm | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-10-14 16:00:53October 14, 2023 | San Juan North Secondary vs Naparima College | 0 - 0 | Premiership | 2023 | San Juan North Secondary School | Recap |
| 2023-10-14 16:00:41October 14, 2023 | Pleasantville Secondary vs Malick Secondary | 0 - 6 | Premiership | 2023 | Manny Ramjohn T. Field | Recap |
| 2023-10-14 16:00:28October 14, 2023 | Presentation College vs Trinity College East | 3 - 0 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-14 16:00:21October 14, 2023 | Fatima College vs Arima North Secondary | 2 - 0 | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-10-14 16:00:08October 14, 2023 | Chaguanas North Secondary vs St. Benedict's College | 0 - 6 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-14 15:30:51October 14, 2023 | St. Mary's College vs Speyside Secondary | 0 - 0 | Premiership | 2023 | St Mary's College Grounds | Recap |
| 2023-10-14 15:30:16October 14, 2023 | Queen's Royal College vs East Mucurapo Secondary | 2 - 2 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-10-14 15:30:15October 14, 2023 | Bishop's High School vs St. Anthony's College | 0 - 3 | Premiership | 2023 | Plymouth Rec. Ground | Recap |
| 2023-10-11 16:00:00October 11, 2023 |  Trinity College East vs St. Mary’s College | 3 - 0 | Premiership | 2023 | Trinity College East | Recap |
| 2023-10-11 16:00:00October 11, 2023 | St. Benedict’s College vs Presentation College | 3 - 0 | Premiership | 2023 | Mannie Ramjohn | Recap |
| 2023-10-11 16:00:00October 11, 2023 | St. Anthony’s College vs Malick Secondary | 2 - 2 | Premiership | 2023 | St. Anthony’s College | Recap |
| 2023-10-11 16:00:00October 11, 2023 | Pleasantville Secondary vs Chaguanas North Secondary | 2 - 0 | Premiership | 2023 | Manny Ramjohn T. Field | Recap |
| 2023-10-11 16:00:00October 11, 2023 | Arima North Secondary vs East Mucurapo Secondary | 0 - 0 | Premiership | 2023 | Arima Velodrome | Recap |
| 2023-10-11 15:30:00October 11, 2023 | Speyside Secondary vs San Juan North Secondary | 0 - 4 | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-10-11 15:30:00October 11, 2023 | Naparima College vs Bishop’s High School | 4 - 0 | Premiership | 2023 | Lewis Street | Recap |
| 2023-10-11 15:30:00October 11, 2023 | Fatima College vs Queen’s Royal College | 7 - 1 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-10-07 16:00:58October 7, 2023 | Pleasantville Secondary vs Arima North Secondary | 0 - 1 | Premiership | 2023 | Yolande Pompey Recreational Grounds | Recap |
| 2023-10-07 16:00:56October 7, 2023 | Chaguanas North Secondary vs Fatima College | 1 - 4 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-10-07 16:00:50October 7, 2023 | Malick Secondary vs St. Mary's College | 5 - 2 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-10-07 16:00:45October 7, 2023 | Naparima College vs Trinity East College | 2 - 1 | Premiership | 2023 | Lewis Street | Recap |
| 2023-10-07 16:00:21October 7, 2023 | Presentation College vs Queen's Royal College | 2 - 0 | Premiership | 2023 | | Recap |
| 2023-10-07 16:00:07October 7, 2023 | East Mucurapo Secondary vs St. Anthony's College | 0 - 2 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-10-07 15:30:25October 7, 2023 | St. Benedict's vs Speyside Secondary | 5 - 0 | Premiership | 2023 | | Recap |
| 2023-10-07 15:30:21October 7, 2023 | San Juan North Secondary vs Bishop's High School | 6 - 0 | Premiership | 2023 | San Juan North Secondary School | Recap |
| 2023-10-04 16:00:00October 4, 2023 | St. Anthony’s College vs Pleasantville Secondary | 6 - 1 | Premiership | 2023 | St. Anthony’s College | Recap |
| 2023-10-04 16:00:00October 4, 2023 | San Juan North Secondary vs Trinity College East | 2 - 1 | Premiership | 2023 | San Juan North Sec. | Recap |
| 2023-10-04 16:00:00October 4, 2023 | Queen’s Royal College vs Chaguanas North Secondary | 6 - 0 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-10-04 16:00:00October 4, 2023 | Malick Secondary vs Arima North Secondary | 1 - 2 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-10-04 16:00:00October 4, 2023 | Fatima College vs Presentation College | 0 - 1 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-10-04 15:30:00October 4, 2023 | Naparima Boys College vs St Benedict’s College | 2 - 3 | Premiership | 2023 | Lewis Street | Recap |
| 2023-10-04 15:30:00October 4, 2023 | Bishop’s High School vs St. Mary’s College | 2 - 3 | Premiership | 2023 | Plymouth Rec. Ground | Recap |
| 2023-10-04 15:30:00October 4, 2023 | Speyside Secondary vs East Mucurapo Secondary | 2 - 1 | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-09-27 16:00:00September 27, 2023 | St. Mary’s College vs East Mucurapo Secondary | 3 - 2 | Premiership | 2023 | St. Mary’s Ground | Recap |
| 2023-09-27 16:00:00September 27, 2023 | Pleasantville Secondary vs Trinity College East | 2 - 2 | Premiership | 2023 | Yolande Pompey Recreational Grounds | Recap |
| 2023-09-27 16:00:00September 27, 2023 | Naparima Boys College vs Malick Secondary | 3 - 0 | Premiership | 2023 | Lewis Street | Recap |
| 2023-09-27 16:00:00September 27, 2023 | Arima North Secondary vs San Juan North Secondary | 0 - 1 | Premiership | 2023 | Arima Velodrome | Recap |
| 2023-09-27 16:00:00September 27, 2023 | Fatima College vs St Benedict’s College | 0 - 0 | Premiership | 2023 | Fatima Ground | Recap |
| 2023-09-27 16:00:00September 27, 2023 | Chaguanas North Secondary vs St. Anthony’s College | 1 - 10 | Premiership | 2023 | Edinburgh 500 | Recap |
| 2023-09-27 15:30:00September 27, 2023 | Speyside Secondary vs Presentation College | 1 - 1 | Premiership | 2023 | Speyside Rec. Ground | Recap |
| 2023-09-27 15:30:00September 27, 2023 | Queen’s Royal College vs Bishop’s High School | 0 - 1 | Premiership | 2023 | Queen’s Royal College | Recap |
| 2023-09-24 16:00:59September 24, 2023 | Queen's Royal College vs San Juan North Secondary | 1 - 2 | Premiership | 2023 | | Recap |
| 2023-09-24 16:00:50September 24, 2023 | Chaguanas North Secondary vs Presentation College | 0 - 3 | Premiership | 2023 | | Recap |
| 2023-09-24 16:00:45September 24, 2023 | St. Benedict's College vs Arima North Secondary | 1 - 1 | Premiership | 2023 | | Recap |
| 2023-09-24 16:00:28September 24, 2023 | East Mucurapo Secondary vs Naparima College | 0 - 7 | Premiership | 2023 | Trinity College East | Recap |
| 2023-09-24 16:00:12September 24, 2023 |  St. Anthony's College vs St. Mary's College | 3 - 0 | Premiership | 2023 | | Recap |
| 2023-09-24 16:00:07September 24, 2023 | Fatima College vs Pleasantville Secondary | 5 - 0 | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-09-24 15:30:31September 24, 2023 | Malick Secondary vs Speyside Secondary | 1 - 2 | Premiership | 2023 | St Mary's College Grounds | Recap |
| 2023-09-13 17:00:00September 13, 2023 | Speyside Secondary vs Bishop’s High School | 3 - 1 | Premiership | 2023 | Dwight Yorke Stadium | Recap |
| 2023-09-13 15:30:00September 13, 2023 | Trinity College East vs East Mucurapo Secondary | 1 - 2 | Premiership | 2023 | Trinity College East | Recap |
| 2023-09-13 15:30:00September 13, 2023 | San Juan North Secondary vs St Benedict’s College | 4 - 3 | Premiership | 2023 | San Juan North Secondary School | Recap |
| 2023-09-13 15:30:00September 13, 2023 | PSS vs SMC | 0 - 8 | Premiership | 2023 | Yolande Pompey Recreational Grounds | Recap |
| 2023-09-13 15:30:00September 13, 2023 | Naparima Boys College vs Chaguanas North Secondary | 10 - 0 | Premiership | 2023 | Lewis Street | Recap |
| 2023-09-13 15:30:00September 13, 2023 | Arima North Secondary vs Presentation College | 0 - 0 | Premiership | 2023 | Arima Velodrome | Recap |
| 2023-09-13 15:30:00September 13, 2023 | Malick Secondary vs QRC | 3 - 1 | Premiership | 2023 | St Mary's College Grounds | Recap |
| 2023-09-13 15:30:00September 13, 2023 | Fatima College vs St. Anthony’s College | 7 - 0 | Premiership | 2023 | Fatima College Sports Grounds | Recap |
| 2023-09-09 16:00:30September 9, 2023 | Fatima College vs St Benedict’s College | 3 - 4 | Premiership | 2023 | Hasely Crawford Stadium | Recap |
