| Play-off | 0 | Friday, 7th June 2019 | 3.30 pm | Queen’s College | Alleyne School | 3:0 | QC: Naiff Lynch, Diego Fenty, Jordon Bryan; RC: Christyion Griffith (ALL) |
| Quarter-finals | 1 | Friday, 14th June 2019 | 1.30 pm | Harrison College | Alexandra School | 3:1 | HC: Spencer Haslett, Matthieu Clarke, Rashawn Batson: AX: Tashawn Nurse |
| Quarter-finals | 2 | Friday, 14th June 2019 | 2.30 pm | Deighton Griffith Secondary School | Queen’s College | 0:0 (3:5 PSO) | |
| Quarter-finals | 3 | Monday, 17th June 2019 | 3.30 pm | Christ Church Foundation School | Pinehill St. Leonard’s Boys’ Secondary School | 1:0 | CCFS: Jaylen Phillips |
| Quarter-finals | 4 | Tuesday, 18th June 2019 | 3.30 pm | The St. Michael School | The Lodge School | 1:1 (4:5 PSO) | SMS: Ziko Ifill; LOD: 19' Tyreke Gittens |
| Semi-finals | 5 | Friday, 21st June 2019 | 1.30 pm | Harrison College | Queen’s College | 1:4 | QC: Nathan Scott (4) |
| Semi-finals | 6 | Friday, 21st June 2019 | 2.30 pm | Christ Church Foundation School | The Lodge School | 2:1 | CCFS: Jalen Johnson, Jaylen Phillips; LOD: Ross Bourne |
| Final | 7 | Friday, 28th June 2019 | 2.30 pm | Queen’s College | Christ Church Foundation School | 2:1 | |
