| Quarter-finals | 1 | Friday, 29th June 2018 | 3.30 pm | The Lodge School | Coleridge and Parry School | 0:5 | CPS: Khimani Cox (4), Nathan Grazette (1) |
| Quarter-finals | 2 | Friday, 29th June 2018 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | The Lester Vaughan School | 2:0 | |
| Quarter-finals | 3 | Friday, 29th June 2018 | 3.30 pm | Queen’s College | Deighton Griffith Secondary School | 6:2 | DGSS: Shamari Harewood, Zion Mayers |
| Quarter-finals | 4 | Tuesday, 3rd July 2018 | 1.00 pm | The St. Michael School | Alexandra School | 3:0* | by forfeit |
| Semi-finals | 5 | Wednesday, 4th July 2018 | 02/01/1900 | The St. Michael School | Queen’s College | 2:1 | TSMS: Josiah Parris, Jaquan Pilgrim; |
| Semi-finals | 6 | Tuesday, 3rd July 2018 | 2.00 pm | Pinehill St. Leonard’s Boys’ Secondary School | Coleridge and Parry School | 0:0 (6:7 PSO) | Annotation: a total of 26 penalties were taken to decide that game |
| Final | 7 | Monday, 8th October 2018 | 3.30 pm | The St. Michael School | Coleridge and Parry School | 1:2 | TSMS: 8' Jaquan Pilgrim (1:0); CPS: 22' Rivaldo Massiah (1:1), 53' Khimani Cox (1:2, PK) |
