| 1 | 1 | Wednesday, 29th October 2014 | 3.30 pm | Graydon Sealy Secondary School | The Lodge School | 1:2 | |
| 1 | 2 | Friday, 31st October 2014 | 3.30 pm | Dacosta Mannings Combermere School | Alexandra School | 0:0 (PSO 4:2) | DMCS: Alex Fergusson, Revaldo Gryton, Avery Chandler, Najee Holder; AXS: Lashan Callender, Micah Boyce |
| 2 | 3 | Monday, 3rd November 2014 | 3.30 pm | Christ Church Foundation School | Queen’s College | 2:0 | CCFS: 24' J. Howard, 77' L. Callender |
| 2 | 4 | Monday, 3rd November 2014 | 3.30 pm | The Lodge School | Darryl Jordan Secondary School | 3:0 | TLS: Ajani Pierce, Marco St. Hill, Ashad Stuart |
| 2 | 5 | Monday, 3rd November 2014 | 3.30 pm | Alleyne School | Deighton Griffith Secondary School | 1:0 | |
| 2 | 6 | Monday, 3rd November 2014 | 3.30 pm | Barbados Community College | The St. Michael School | 2:0 | BCC: Nicholas Jones (2) |
| 2 | 7 | Monday, 3rd November 2014 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Frederick Smith Secondary School | 1:2 | |
| 2 | 8 | Monday, 3rd November 2014 | 3.30 pm | Harrison College | Tang Parkinson Memorial Secondary School | 5:1 | HC: 24' Raheim Hinds (1:0), 30' Jaden Norville (2:0) 32' Stephan Seale (3:0), 51' Javon Medford (4:0), 54' Stephan Seale (5:0); TPMSS: 73' Lamario Springer (5:1) |
| 2 | 9 | Friday, 7th November 2014 | 3.30 pm | The Lester Vaughan School | Princess Margaret Secondary School | 3:5 | TLVS: 12' Antonio Weekes (1:0), 35' Antonio Weekes (2:2), 70' Omani Leacock (3:4); PMSS: 16' Jarad Hepburn (1:1), 21' Hakeem Field (1:2), 55' Daniel Wilkinson (2:3), 63' Daniel Wilkinson (2:4), 78' Kale Greenidge (3:5) |
| 2 | 10 | Monday, 3rd November 2014 | 3.30 pm | Coleridge and Parry School | Dacosta Mannings Combermere School | 1:0 | CPS: Natari Worrell |
| 3 | 11 | Friday, 28th November 2014 | 3.30 pm | Christ Church Foundation School | The Lodge School | 0:1 | TLS: 3' Stefan Watson (0:1); Red Card: Javan Dowridge (CCFS) |
| 3 | 12 | Friday, 28th November 2014 | 3.30 pm | Alleyne School | Barbados Community College | 1:4 | AS: 70' Akio Bartlett (1:2, PK); BCC: 39' Nicholas Jones (0:1), 45' Nicholas Jones (0:2), 75' Ramon Collmore (1:3), 79' Nicholas Jones (1:4, PK) |
| 3 | 13 | Friday, 14th November 2014 | 3.30 pm | Frederick Smith Secondary School | Harrison College | 3:1 | FSSS: Rasheed Boyce (2), Kadeem Atwell (1); HC: Carl Hinkson |
| 3 | 14 | Friday, 14th November 2014 | 3.30 pm | Princess Margaret Secondary School | Coleridge and Parry School | 2:3 | PMSS: Daniel Wilkinson, Nathaniel Springer; CPS: Torrell Jemmott, Natari Worrell, Shaquan Griffith |
| SEMI-FINALS | 15 | Tuesday, 2nd December 2014 | 3.30 pm | The Lodge School | Barbados Community College | 0:1 | BCC: 79' Rashad Jones (0:1) |
| SEMI-FINALS | 16 | Wednesday, 3rd December 2014 | 3.30 pm | Frederick Smith Secondary School | Coleridge and Parry School | 0:1 | CPS: 80' Natari Worrell (0:1) |
| FINAL | 17 | Friday, 6th February 2015 | 3.30 pm | Barbados Community College | Coleridge and Parry School | 1:2 | BCC: Renaldo Bailey; CPS: Nadico Smith, Darion Scantlebury |
