| 1 | Friday, 14th October 2016 | 3.30pm | The Lester Vaughan School | Combermere School | 3:0 | TLVS: Akil Alleyne (2), Kashane Burgess-Grandison (1) |
| 1 | Friday, 28th October 2016 | 3.30pm | Queen’s College | Barbados Community College | 2:1 | QC: 9' Alex Atherley (1:0), 44' Andre Cumberbatch (2:0); BCC: 64' Tyrrell Bancroft (2:1); RC (2 x YC 70', 78'): Shaquan Griffith (BCC) |
| 1 | Friday, 14th October 2016 | 3.30pm | Alexandra School | Harrison College | 4:2 | AXS: Micah Boyce (2), Javier Nedd (1), Nicolai Jackman (1); HC: Rashawn Thomas, Tyrique Jones |
| 1 | Friday, 28th October 2016 | 3.30pm | The Lodge School | Christ Church Foundation School | 2:1 | TLS: Marco St.Hill, Roshon Gittens; CCFS: Joshua Browne |
| 2 | Wednesday, 12th October 2016 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Queen’s College | 2:0 | PSLBSS: Rashad Grant, Dishon Howell |
| 2 | Wednesday, 12th October 2016 | 3.30pm | Harrison College | The Lester Vaughan School | 2:4 | HC: Tyrique Jones, Darien Marshall; TLVS: Kashane Burgess (2), Zuri Jones (1), Sheran Hoyte (1) |
| 2 | Wednesday, 12th October 2016 | 3.30pm | Barbados Community College | The Lodge School | 2:2 | TLS: Marco St.Hill, Jamali Lynch |
| 2 | Friday, 4th November 2016 | 3.30pm | Christ Church Foundation School | Alexandra School | 2:1 | CCFS: Cliff Gooding-Edgehill, Deshawn Trent; AXS: Nikolai Jackman; RC: Paul Doughty, John Ruck |
| 3 | Monday, 17th October 2016 | 3.30pm | Combermere School | Harrison College | 3:0 | CS: Zidane Clarke (2), Denilson Harte (1) |
| 3 | Monday, 17th October 2016 | 3.30pm | The Lodge School | Pinehill St. Leonard’s Boys’ Secondary School | 0:5 | PSLBSS: Rashad Grant, Shakiel James, Avery Chandler, Niall Reid-Stephens, Jaiden Miller |
| 3 | Monday, 17th October 2016 | 3.30pm | The Lester Vaughan School | Christ Church Foundation School | 0:0 | |
| 3 | Monday, 17th October 2016 | 3.30pm | Alexandra School | Barbados Community College | 0:0 | |
| 4 | Friday, 4th November 2016 | 3.30pm | Queen’s College | The Lodge School | 1:4 | QC: 39' Alex Atherley (1:1); TLS: 11' Marco St.Hill (0:1), 43' Daniel Hinds (1:2), 68' Jamanni Brathwaithe (1:3), 70' Jamali Lynch (1:4) |
| 4 | Wednesday, 19th October 2016 | 3.30pm | Christ Church Foundation School | Combermere School | 5:1 | CCFS: Deshawn Trent (3), Natari Worrell (2); CS: Kobia Hamblin |
| 4 | Wednesday, 19th October 2016 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Alexandra School | 2:0 | PSLBSS: Rashad Grant, Niall Reid-Stephens |
| 4 | Wednesday, 19th October 2016 | 3.30pm | Barbados Community College | The Lester Vaughan School | 1:0 | BCC: Zaquan Ishmael; RC: Chris Williams (BCC) |
| 5 | Monday, 24th October 2016 | 3.30pm | Christ Church Foundation School | Harrison College | 4:3 | CCFS: Natari Worrell (2), Jaheim Grant (1), Cliff Gooding-Edgehill (1); |
| 5 | Monday, 24th October 2016 | 3.30pm | Queen’s College | Alexandra School | 3:1 | QC: Belle, Jeremiah McCollin, Quintyn Walcott; AXS: Micah Boyce |
| 5 | Friday, 4th November 2016 | 3.30pm | Barbados Community College | Combermere School | 2:2 | CS: Maxwell Lewis, Shaquille Harewood; RC: Zachary Bellamy (CS) |
| 5 | Monday, 24th October 2016 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | The Lester Vaughan School | 4:1 | PSLBSS: Niall Reid-Stephens (2), Avery Chandler (1), Rashaad Philips (1); TLVS: Quamie Neblett |
| 6 | Wednesday, 26th October 2016 | 3.30pm | Alexandra School | The Lodge School | 2:1 | AXS: Micah Boyce, Mattiel Williams; TLS: Marco St.Hill |
| 6 | Wednesday, 26th October 2016 | 3.30pm | Harrison College | Barbados Community College | 0:0 | |
| 6 | Wednesday, 26th October 2016 | 3.30pm | The Lester Vaughan School | Queen’s College | 3:2 | TLVS: Sheran Hoyte (PK), Jafari Marshall, Akil Alleyne; QC: 52' Alex Atherley, 81' Dario Greaves |
| 6 | Wednesday, 2nd November 2016 | 3.30pm | Combermere School | Pinehill St. Leonard’s Boys’ Secondary School | 0:5 | PSLBSS: Rashad Grant (2), Dishon Howell (1), Thierry Gale (1), Rashaad Philips (1) |
| 7 | Monday, 7th November 2016 | 3.30pm | Barbados Community College | Christ Church Foundation School | 2:1 | CCFS: Jaedon Moore |
| 7 | Monday, 7th November 2016 | 3.30pm | The Lodge School | The Lester Vaughan School | 2:1 | TLS: Marco St.Hill, Jamali Lynch; TLVS: Zuri Jones |
| 7 | Friday, 25th November 2016 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Harrison College | 3:0* | by forfeit |
| 7 | Friday, 25th November 2016 | 3.30pm | Queen’s College | Combermere School | 0:2 | CS: Maxwell Lewis, Rivaldo Graham |
| 8 | Wednesday, 9th November 2016 | 3.30pm | The Lester Vaughan School | Alexandra School | 3:2 | TLVS: 2' Quamie Neblett (1:0), 33' Damar Maloney (2:1, PK), 71' Damar Maloney (3:2); AXS: 39' Javier Nedd (1:1), 65' Thai Moore (2:2) |
| 8 | Wednesday, 9th November 2016 | 3.30pm | Christ Church Foundation School | Pinehill St. Leonard’s Boys’ Secondary School | 0:1 | |
| 8 | Wednesday, 9th November 2016 | 3.30pm | Combermere School | The Lodge School | 3:0* | by forfeit |
| 8 | Wednesday, 9th November 2016 | 3.30pm | Harrison College | Queen’s College | 0:3 | QC: Alex Atherley, Quintyn Walcott, Ethan Bryan |
| 9 | | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Barbados Community College | | |
| 9 | Monday, 5th December 2016 | 3.30pm | Alexandra School | Combermere School | 4:3 | AXS: Micah Boyce (3), Russell Taylor; CS: Maxwell Lewis, Zidane Clarke, Dante Niles |
| 9 | Tuesday, 22nd November 2016 | 3.30pm | Queen’s College | Christ Church Foundation School | 1:1 | QC: Tre Mottley; CCFS: Cliff Gooding-Edgehill |
| 9 | | 3.30pm | The Lodge School | Harrison College | 1:1 | TLS: Dejuan Walcott; HC: Kyle Hinkson |
