| 1 | Wednesday, 14th May 2014 | 3.30 pm | Harrison College | Ellerslie Secondary School | 3:0 | HC: 4' Reshawn Thomas (1:0), 24' own goal ESS (2:0), 28' Reshawn Thomas (3:0) |
| 1 | Friday, 23rd May 2014 | 3.30 pm | The Lester Vaughan School | Combermere School | 0:1 | CS: Zidane Clarke |
| 1 | Friday, 23rd May 2014 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | St. George Secondary School | 1:1 | PSLBSS: Janeico Baptiste; SGSS: Tyrese Brathwaite |
| 2 | Friday, 16th May 2014 | 3.30 pm | Combermere School | Harrison College | 0:0 | |
| 2 | Friday, 16th May 2014 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Ellerslie Secondary School | 5:1 | PSLBSS: 6' Donte Greenidge (1:0), 10' Kobe Griffith (2:0), 21' Deroni Hurley (3:0), 39' Dishon Howell (4:1), 43' Thierry Gale (5:1); ESS: 37' Terry Graham (3:1) |
| 2 | Friday, 16th May 2014 | 3.30 pm | The Lester Vaughan School | St. George Secondary School | 1:1 | |
| 3 | Monday, 19th May 2014 | 3.30 pm | Harrison College | Pinehill St. Leonard’s Boys’ Secondary School | 0:3 | PSLBSS: Donte Greenidge (3) |
| 3 | Monday, 19th May 2014 | 3.30 pm | Combermere School | St. George Secondary School | 4:2 | CS: Zidane Clarke (2), Dicarlo Cox, Aarin Wiltshire; SGSS: Tranniko Browne (2) |
| 3 | Wednesday, 4th June 2014 | 3.30 pm | Ellerslie Secondary School | The Lester Vaughan School | 0:3* | * by default |
| 4 | Wednesday, 21st May 2014 | 3.30 pm | St. George Secondary School | Harrison College | 1:1 | SGSS: Nicholas Ellis; HC: Reshawn Thomas |
| 4 | Wednesday, 21st May 2014 | 3.30 pm | The Lester Vaughan School | Pinehill St. Leonard’s Boys’ Secondary School | 0:3 | PSLBSS: Deroni Hurley, Donte Greenidge, Thierry Gale |
| 4 | Wednesday, 21st May 2014 | 3.30 pm | Ellerslie Secondary School | Combermere School | 0:3 | CS: 11' Zidane Clarke (0:1), 40' Dicarlo Cox (0:2), 50' Ramon Toppin (0:3) |
| 5 | Monday, 26th May 2014 | 3.30 pm | Harrison College | The Lester Vaughan School | 1:0 | HC: Harley Moseley |
| 5 | Monday, 26th May 2014 | 3.30 pm | St. George Secondary School | Ellerslie Secondary School | 2:0 | SGSS: 33' Rico Baker (1:0), 46' Rico Baker (2:0) |
| 5 | Monday, 26th May 2014 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Combermere School | 4:1 | PSLBSS: Thierry Gale (2), Deroni Hurley, Dishon Howell; CS: Darian Padmore |
