| 1 | Monday, 13th May 2019 | 3.30 pm | Alleyne School | Alexandra School | 1:0 | |
| 1 | Friday, 31st May 2019 | 3.30 pm | Frederick Smith Secondary School | Coleridge and Parry School | 0:4 | CP: Rovaldo Massiah (2), Requan Browne (1), Joshua Husbands (1) |
| 2 | Monday, 27th May 2019 | 3.30 pm | Coleridge and Parry School | Alexandra School | 1:2 | CP: 36' Zavier Williams (1:2); AX: 5' Dontae Cumberbatch (0:1), 28' Tashawn Nurse (0:2) |
| 2 | Wednesday, 15th May 2019 | 3.30 pm | Queen’s College | Frederick Smith Secondary School | 0:0 | |
| 3 | Wednesday, 29th May 2019 | 3.30 pm | Coleridge and Parry School | Alleyne School | 1:1 | CP: Rovaldo Massiah; ALL: Kiko Wade (PK) |
| 3 | Friday, 17th May 2019 | 3.30 pm | Alexandra School | Queen’s College | 1:1 | AX: Dontae Cumberbatch (PK); QC: Naiff Lynch |
| 4 | Friday, 24th May 2019 | 3.30 pm | Frederick Smith Secondary School | Alleyne School | 1:1 | FSSS: 11' Kemar Smith (1:0), ALL: 34' Kiko Wade (1:1) |
| 4 | Monday, 20th May 2019 | 3.30 pm | Queen’s College | Coleridge and Parry School | 2:1 | QC: Diego Fenty (PK), Jaylan Williams; CP: Rovaldo Massiah |
| 5 | Wednesday, 22nd May 2019 | 3.30 pm | Alleyne School | Queen’s College | 2:2 | ALL: Dandre Mitchell (2); QC: Caleb Williams, Kiron Quimby |
| 5 | Wednesday, 29th May 2019 | 3.30 pm | Frederick Smith Secondary School | Alexandra School | 0:3 | AX: 33' Dontae Cumberbatch (0:1), 47' Tashawn Nurse (0:2), 51' Jamali Morgan (0:3) |
