| Playoff | 1 | Monday, 20th February 2017 | 3.30 pm | Coleridge and Parry School | Tang Parkinson Memorial Secondary School | - | Tang Parkinson Memorial Secondary School withdrew from the competition |
| Playoff | 2 | Monday, 20th February 2017 | 3.30 pm | The Lester Vaughan School | Pinehill St. Leonard’s Boys’ Secondary School | 1:3 | |
| 1 | 3 | Wednesday, 8th March 2017 | 3.30 pm | St. George Secondary School | Coleridge and Parry School | 1:1 (PSO 4:2) | SGSS: 50' Jamarko Gill (1:1); CPS: 46' Tyreses Gonzales |
| 1 | 4 | Friday, 24th February 2017 | 3.30 pm | Graydon Sealy Secondary School | Combermere School | 0:2 | CS: Paul Clarke, Nathan Skeete |
| 1 | 5 | Friday, 3rd March 2017 | 3.30 pm | Deighton Griffith Secondary School | Queen’s College | 1:1 (PSO 5:4) | DGSS: 15' Sylvan Wade (1:0); QC: 43' Pierre Harding (1:1); PSO DGSS: Raudniaco Holder, Malique Jones, Sylvan Wade, Jaquan Sergeant, Jamani Moore; |
| 1 | 6 | Monday, 20th February 2017 | 3.30 pm | The Lodge School | Harrison College | 5:0 | TLS: 6' Triston Bancroft (1:0), 22' Aaron Ward (2:0), 24' Nathan Scott (3:0), 55' Aaron Ward (4:0), 56' Dejuan Walcott (5:0) |
| 1 | 7 | Monday, 20th February 2017 | 3.30 pm | Ellerslie Secondary School | Pinehill St. Leonard’s Boys’ Secondary School | 0:3* | * by forfeit |
| 1 | 8 | Wednesday, 8th March 2017 | 3.30 pm | St. Winifred’s School | Frederick Smith Secondary School | 1:2 | SWS: 20' Drew Brooks (1:0); FSSS: 33' Shaquan Lemming (1:1), 50' Shaquan Lemming (1:2) |
| 1 | 9 | Monday, 20th February 2017 | 3.30 pm | Princess Margaret Secondary School | Alexandra School | 0:6 | AXS: Aaron Cumberbatch (2), Antonio Broomes (1), Raheem Archer (1), Keron Worrell (1), Alec Kellman (1) |
| 1 | 10 | Monday, 20th February 2017 | 3.30 pm | Christ Church Foundation School | The St. Michael School | 6:0 | CCFS: Saviola Thomas (3), Tajio James (1), Ari Dorson (1), Kelon Carrington (1) |
| QUARTER-FINALS | 11 | Friday, 10th March 2017 | 3.30 pm | St. George Secondary School | Combermere School | 0:3 | CS: Andre Applewaithe, Christian John, Devonte Richards |
| QUARTER-FINALS | 12 | Wednesday, 8th March 2017 | 3.30 pm | Deighton Griffith Secondary School | The Lodge School | 1:3 | DGSS: Sylvan Wade; TLS: Roshon Gittens, Devon Wiltshire, Jadon Pitt |
| QUARTER-FINALS | 13 | Wednesday, 8th March 2017 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Frederick Smith Secondary School | - | |
| QUARTER-FINALS | 14 | Wednesday, 8th March 2017 | 3.30 pm | Alexandra School | Christ Church Foundation School | 3:2 | AXS: Nazario Adamson, Jaylen Gilkes (PK), Nathanial Knight; CCFS: Ari Dorson, Saviola Thomas |
| SEMI-FINALS | 15 | Wednesday, 15th March 2017 | 3.30 pm | Combermere School | The Lodge School | 2:1 | CS: Devonte Richards, Andre Applewaithe |
| SEMI-FINALS | 16 | Friday, 5th May 2017 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Alexandra School | 3:1 | PSLBSS: 13' Thierry Gale (1:0), 56' Thierry Gale (2:1), 59' Tyrek King (3:1); AXS: 24' Jaylen Gilkes (1:1) |
| FINAL | 17 | Monday, 8th May 2017 | 3.00 pm | Combermere School | Pinehill St. Leonard’s Boys’ Secondary School | 0:1 | PSLBSS: 39' Thierry Gale (0:1) |
