| Quarter-final | Monday, 5th May 2014 | 3.30 pm | Christ Church Foundation School | Parkinson Memorial Secondary School | 4:1 | CCFS: Juwon Walcott (2), Antone Greaves (2); PMSS: Quashad Harewood |
| Quarter-final | Monday, 5th May 2014 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Grantley Adams Memorial School | 1:0 | PSLBSS: Djidad Forde |
| Quarter-final | Wednesday 7th May 2014 | 3.30 pm | Frederick Smith Secondary School | Alleyne School | 2:0 | FSSS: Kavian Inniss, Sachin Corbin |
| Quarter-final | Wednesday 7th May 2014 | 3.30 pm | Alexandra School | Harrison College | 4:0 | AXS: Gavin Sandiford (2), Micah Boyce (penalty), Shacolby Corbin |
| Semi final | Friday 9th May 2014 | 3.30 pm | Frederick Smith Secondary School | Christ Church Foundation School | 1:0 | FSSS: 48' Kavian Inniss (1:0) |
| Semi final | Friday 9th May 2014 | 3.30 pm | Alexandra School | Pinehill St. Leonard’s Boys’ Secondary School | 0:1 | PSLBSS: Kyle Bascombe Browne |
| 3rd place | Thursday, 15th May 2014 | 2.30 pm | Alexandra School | Christ Church Foundation School | 1:0 | AXS: 50' Russell Taylor (1:0) |
| Final | Thursday, 15th May 2014 | 3.45 pm | Frederick Smith Secondary School | Pinehill St. Leonard’s Boys’ Secondary School | 2:2 (4:5p) | FSSS: 43' Ronnie Farley (1:2), 70' Ronnie Farley (2:2); PSLBSS: 16' Christopher Shepherd (0:1), 25' Chrishawn Browne (0:2) |
| | | | | Penalties: | FSSS: Ridon Pilgrim, Kemal Haynes, Kavian Inniss, Akeem Welch |
| | | | | | PSLBSS: Kobe Bell, Rashad Crichlow, Christopher Shepherd, Djidad Forde, Rashon Crichlow |
