| Pre | 1 | Wednesday, 5th October 2016 | 3.30 pm | Christ Church Foundation School | The Lester Vaughan School | 3:4 PSO | |
| Pre | 2 | Friday, 7th October 2016 | 3.30 pm | Queen’s College | The Lodge School | 1:0 | QC: Alex Atherley |
| 1 | 3 | Friday, 11th November 2016 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | The Lester Vaughan School | 2:0 | |
| 1 | 4 | Monday, 31st October 2016 | 3.30 pm | Coleridge and Parry School | Alexandra School | 1:3 | AXS: Micah Boyce (0:1), Micah Boyce (PK, 0:2), Deshawn Toppin (1:3); CPS: Enrique Babb (1:2) |
| 1 | 5 | Monday, 31st October 2016 | 3.30 pm | Samuel Jackman Prescod Polytechnic | Combermere School | 3:0 | SJPP: 27' Ray Francis (1:0), 60' Josiah Hinds (2:0), 71' Josiah Hinds (3:0) |
| 1 | 6 | Monday, 31st October 2016 | 3.30 pm | Tang Parkinson Memorial Secondary School | The St. Michael School | 2:2 (PSO 1:4) | TPMSS: Shaquon Tull (2); TSMS: Tomar Haynes, Aluko Callender |
| 1 | 7 | Monday, 31st October 2016 | 3.30 pm | Barbados Community College | Queen’s College | 0:3* | by default |
| 1 | 8 | Wednesday, 2nd November 2016 | 3.30 pm | Deighton Griffith Secondary School | St. George Secondary School | 2:3 | SGSS: Shavonne Jones (2), Ngozi Reid (1) |
| 1 | 9 | Wednesday, 2nd November 2016 | 3.30 pm | Barbados Vocational Training Board | Harrison College | 4:1 | BVTB: Kavian Inniss (3), Rickneco Marshall (1, PK) |
| 1 | 10 | Wednesday, 2nd November 2016 | 3.30 pm | Ellerslie Secondary School | Princess Margaret Secondary School | 6:0 | ESS: 34' Jameel Walkes-Miller (1:0), 35' Xario Prescod (2:0), 44' Tresanee Goodridge (3:0), 50' Jameel Walkes-Miller (4:0), 60' Tresanee Goodridge (5:0), 70' Terry Rollock (6:0) |
| 2 | 11 | Friday, 18th November 2016 | 2.00 pm | Pinehill St. Leonard’s Boys’ Secondary School | Alexandra School | 3:1 | PSLBSS: 30' Dishon Howell (1:1), 44' Niall Reid-Stephens (2:1), 71' Thierry Gale (3:1); AXS: 23' Malique Springer (0:1) |
| 2 | 12 | Thursday, 17th November 2016 | 3.30 pm | Samuel Jackman Prescod Polytechnic | The St. Michael School | 4:1 | |
| 2 | 13 | Wednesday, 16th November 2016 | 3.30 pm | Queen’s College | St. George Secondary School | 1:1 (PSO 6:7) | QC: Jeremiah McCollin; SGSS: Ngozi Reid; |
| 2 | 14 | Wednesday, 16th November 2016 | 3.30 pm | Barbados Vocational Training Board | Ellerslie Secondary School | 2:0 | BVTB: Rickneco Marshall (PK), Trevere Allen; |
| SEMI-FINALS | 15 | Wednesday, 23rd November 2016 | 3.00 pm | Pinehill St. Leonard’s Boys’ Secondary School | Samuel Jackman Prescod Polytechnic | 2:2 (PSO 2:3) | PSLBSS: 19' Dishon Howel (1:0), 53' Rashad Philips (2:1); SJPP: 31' Demar Linton (1:1), 76' Demar Linton (2:2) |
| SEMI-FINALS | 16 | Wednesday, 23rd November 2016 | 3.00 pm | St. George Secondary School | Barbados Vocational Training Board | 1:6 | SGSS: Winston Maynard; BVTB: 16' Trevere Allen, 38' Zidan Harewood, 46' Kavian Inniss, 57' Kavian Inniss, 61' Kavian Inniss (PK), 80' Christopher Shepherd; RC: Rickneco Marshall (BVTB) |
| 3rd place | 17 | Wednesday, 14th December 2016 | 2.00 pm | Pinehill St. Leonard’s Boys’ Secondary School | St. George Secondary School | 6:0 | PSLBSS: 7' Niall Reid-Stephens (1:0), 10' Rashaad Philips (2:0), 20' Darrian Croney (3:0), 63' Rashaad Philips (4:0), 64' Terrell Hinds (5:0), 78' Rashaad Philips (6:0) |
| FINAL | 18 | Wednesday, 14th December 2016 | 3.30 pm | Samuel Jackman Prescod Polytechnic | Barbados Vocational Training Board | 4:3 | SJPP: 6' Rashad Crichlow (1:0), 35' Demar Linton (2:2), 68' Josiah Hinds (3:3), 77' Rashad Crichlow (4:3); BVTB: 15' Trevere Allen (1:1), 20' Rickneco Marshall (1:2), 45' Kavian Inniss (2:3) |
