| 1 | 1 | Friday, 26th October 2018 | 3.30 pm | Ellerslie Secondary School | The Lester Vaughan School | 0:4 | |
| 1 | 2 | Friday, 26th October 2018 | 3.30 pm | Barbados Vocational Training Board | Christ Church Foundation School | 2:0 | BVTB: Coby Mayers, Drewmar Gittens |
| 1 | 3 | Friday, 2nd November 2018 | 3.30 pm | Combermere School | Daryll Jordan Secondary School | 2:0 | CS: 21' Nathan Skeete, 47' |
| 1 | 4 | Friday, 2nd November 2018 | 3.30 pm | St. Winifred's School | Parkinson Memorial Secondary School | 0:3* | * by forfeit |
| 1 | 5 | Friday, 2nd November 2018 | 3.30 pm | Barbados Community College | St. George Secondary School | 6:0 | BCC: Kobe Griffith (2), Zidane Clarke (3), Donte Small (1) |
| 2 | 6 | Friday, 16th November 2018 | 3.30 pm | Alexandra School | The Lester Vaughan School | 4:0 | AX: Romario Drakes (2), Abiola Grant (12), Elijah Cave (1) |
| 2 | 7 | Friday, 9th November 2018 | 3.30 pm | Samuel Jackman Prescod Institute Of Technology | The Lodge School | 1:1 (3:5 PSO) | SJPIT: 46' Dorian Croney (1:0); TLS: 60' Tristan Bancroft (1:1) |
| 2 | 8 | Friday, 9th November 2018 | 3.30 pm | Princess Margaret Secondary School | Barbados Vocational Training Board | 3:3 (1:3 PSO) | PMSS: 2' Nathan McCollin (1:0), 9' Jaquan Callender (2:0), 73' Nathan McCollin (3:3); BVTB: 16' Klelmar Chandler (2:1), 67' Enrique Babb (2:2), 70' Kelmar Chandler (2:3) |
| 2 | 9 | Wednesday, 21st November 2018 | 3.30 pm | Frederick Smith Secondary School | Combermere School | 0:2 | CS: 19' Zachary Bellamy (0:1), 52' Jaylen Gilkes (0:2); RC: Jaylen Gilkes (69', CS) |
| 2 | 10 | Monday, 19th November 2018 | 3.30 pm | Harrison College | Parkinson Memorial Secondary School | 2:2 (4:1 PSO) | |
| 2 | 11 | Wednesday, 31st October 2018 | 3.30 pm | Alleyne School | Deighton Griffith Secondary School | 1:0 | ALL: Noel Gordon |
| 2 | 12 | Friday, 9th November 2018 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Barbados Community College | 3:0* | * by forfeit |
| 2 | 13 | Friday, 9th November 2018 | 3.30 pm | Coleridge and Parry School | Queen’s College | 2:2 (3:4 PSO) | CPS: Tyrese Thomas, Javier Smith; QC: Tre Mottley (2) |
| Quarter-Finals | 14 | Wednesday, 21st November 2018 | 3.30 pm | Alexandra School | The Lodge School | 1:2 | AX: 73' Javier Nedd (1:2); TLS: 32' Tristan Bancroft (0:1), 69' Dejuan Walcott (0:2) |
| Quarter-Finals | 15 | Friday, 23rd November 2018 | 3.30 pm | Barbados Vocational Training Board | Combermere School | 0:2 | CS: Zachary Bellamy, Devonte Richards |
| Quarter-Finals | 16 | Wednesday, 21st November 2018 | 3.30 pm | Harrison College | Alleyne School | 1:2 | HC: 5' Rashawn Thomas (1:0); ALL: 15' Jaheim Neblett (1:1, PK), 37' Nadre Butcher (1:2) |
| Quarter-Finals | 17 | Monday, 26th November 2018 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Queen’s College | 3:0 | |
| Semi-Finals | 18 | Wednesday, 28th November 2018 | 2.00 pm | The Lodge School | Combermere School | 0:3 | |
| Semi-Finals | 19 | Wednesday, 28th November 2018 | 3.30 pm | Alleyne School | Pinehill St. Leonard’s Boys’ Secondary School | 1:6 | |
| 3rd place | 20 | Wednesday, 5th December 2018 | 2.00 pm | The Lodge School | Alleyne School | 0:3 | ALL: Davyuan Clarke (2), Jauron Fields (1) |
| Final | 21 | Wednesday, 5th December 2018 | 3.30 pm | Combermere School | Pinehill St. Leonard’s Boys’ Secondary School | 1:2 | |
