| 1 | Wednesday, 2nd October 2019 | 3.30 pm | Christ Church Foundation School | Alexandra School | 1:4 | CCFS: Jalen Johnson; AX: Damario Francis (1), Dontae Cumberbatch (2), Tirell Reece (1) |
| 1 | Wednesday, 2nd October 2019 | 3.30 pm | Combermere School | Queen’s College | 0:3* | * by forfeit |
| 1 | Wednesday, 2nd October 2019 | 3.30 pm | The St. Michael School | Pinehill St. Leonard’s Boys’ Secondary School | 1:3 | SMS: Jaquan Pilgrim; SLB: Joshua Clarke (3) |
| 1 | Wednesday, 2nd October 2019 | 3.30 pm | Harrison College | Deighton Griffith Secondary School | 2:1 | DGSS: 30' Uel White |
| 1 | Friday, 11th October 2019 | 3.30 pm | Alleyne School | The Lodge School | 0:3 | LOD: Shakeri Blades, Edward Downey, Reuben Jacobs |
| 2 | Wednesday, 9th October 2019 | 3.30 pm | The Lodge School | Christ Church Foundation School | 3:0 | LOD: 12' Edward Downey (1:0), 53' Shakeri Blades (2:0), 70' Shakeri Blades (3:0) |
| 2 | Wednesday, 9th October 2019 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Alexandra School | 5:3 | SLB: Joshua Clarke (3), Shamario Marshall (1), Kemar Butler (1); AX: Tirell Reece (2), Dontae Cumberbatch (1) |
| 2 | Wednesday, 9th October 2019 | 3.30 pm | Queen’s College | Alleyne School | 8:0 | QC: Khalil Vanderpool-Nurse (4), Ethan Squires (2), Yanni Marshall (1), OG ALL |
| 2 | Wednesday, 9th October 2019 | 3.30 pm | Deighton Griffith Secondary School | The St. Michael School | 0:2 | SMS: Jaquan Pilgrim, Trevon Cadogan |
| 2 | Monday, 25th November 2019 | 3.30 pm | Harrison College | Combermere School | 1:6 | HC: Azahri Haynes; COM: Marcus Whittington (2), Nataree Boyce-Fitzpatrick (1), Quashaun Lynch (1), Azari Brewster (1), OG HC |
| 3 | Wednesday, 16th October 2019 | 3.30 pm | Christ Church Foundation School | Pinehill St. Leonard’s Boys’ Secondary School | 1:2 | CCFS: Jayden Phillips |
| 3 | Wednesday, 16th October 2019 | 3.30 pm | The Lodge School | Queen’s College | 1:2 | LOD: Shakeri Blades; QC: Ethan Squires, Khalil Vanderpool-Nurse |
| 3 | Friday, 18th October 2019 | 3.30 pm | Alexandra School | Deighton Griffith Secondary School | 1:1 | AX: Myles Brewster |
| 3 | Friday, 18th October 2019 | 3.30 pm | Alleyne School | Harrison College | 3:0 | |
| 3 | Friday, 18th October 2019 | 3.30 pm | The St. Michael School | Combermere School | 1:0 | SMS: Joshua Collymore |
| 4 | Wednesday, 23rd October 2019 | 3.30 pm | Queen’s College | Christ Church Foundation School | 6:1 | QC: Khalil Vanderpool-Nurse (2), Yanni Marshall (1), Kishmar Ramsey (1), Ethan Squires (1), Sayfuddeen Cumberbatch (1); CCFS: Jalen Johnson (PK) |
| 4 | Wednesday, 23rd October 2019 | 3.30 pm | Deighton Griffith Secondary School | Pinehill St. Leonard’s Boys’ Secondary School | 0:7 | SLB: Joshua Clarke (3), Azarian Harewood (2), Kemar Butler (2) |
| 4 | Wednesday, 23rd October 2019 | 3.30 pm | Harrison College | The Lodge School | 3:3 | HC: Ethan Goodridge, Kanye Wharton, Aaron Moore; LOD: Tyreke Gittens, Shakeri Blades, Seth Jervier |
| 4 | Wednesday, 23rd October 2019 | 3.30 pm | Combermere School | Alexandra School | 4:0 | COM: Azari Brewster (2), Ethan Taylor (1), Nataree Boyce-Fitzpatrick (1) |
| 4 | Wednesday, 23rd October 2019 | 3.30 pm | The St. Michael School | Alleyne School | 3:3 | ALL: Thierry Corbin, Dandre Mitchell, Sh'cur Bryant |
| 5 | Wednesday, 6th November 2019 | 3.30 pm | Christ Church Foundation School | Deighton Griffith Secondary School | 3:2 | CCFS: Daniel Thomas (2), Jalen Johnson (1); DGSS: 29' Shamari Harewood, 31' Shamari Harewood |
| 5 | Wednesday, 6th November 2019 | 3.30 pm | Queen’s College | Harrison College | 7:0 | QC: Khalil Vanderpool-Nurse (1), Kishmar Ramsey (1), Jordan Bryan (1), Toby Dottin (1), Khalil Yearwood-Miller (2), OK HC |
| 5 | Monday, 17th February 2020 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Combermere School | 3:0* | * by forfeit |
| 5 | Wednesday, 6th November 2019 | 3.30 pm | The Lodge School | The St. Michael School | 1:0 | |
| 5 | Friday, 31st January 2020 | 3.30 pm | Alexandra School | Alleyne School | 2:0 | AX: Tirell Reece, Rayna Cummins |
| 6 | Wednesday, 27th November 2019 | 3.30 pm | Harrison College | Christ Church Foundation School | 0:2 | CCFS: Kenrian Harris, Jayden Phillips |
| 6 | Wednesday, 20th November 2019 | 3.30 pm | Combermere School | Deighton Griffith Secondary School | 3:5 | COM: Ethan Taylor, Marcus Whittington, OG DGSS; DGSS: Shamari Harewood (2), Akodi Corbin (2), Decode Sealy (1) |
| 6 | Wednesday, 12th February 2020 | 3.30 pm | The St. Michael School | Queen’s College | 1:4 | SMS: Trevon Cadogan; QC: Khalil Vanderpool-Nurse (2), Ethan Squires (1), Jordan Bryan (1) |
| 6 | Wednesday, 12th February 2020 | 3.30 pm | Alleyne School | Pinehill St. Leonard’s Boys’ Secondary School | 0:3* | * by forfeit |
| 6 | Monday, 24th February 2020 | 3.30 pm | Alexandra School | The Lodge School | 2:0 | AX: Tirell Reece, Dontae Cumberbatch |
| 7 | Friday, 31st January 2020 | 3.30 pm | Christ Church Foundation School | Combermere School | 2:1 | CCFS: Jayden Phillips (2) |
| 7 | Wednesday, 15th January 2020 | 3.30 pm | Harrison College | The St. Michael School | 0:5 | SMS: Jaquan Pilgrim (2), Joshua Collymore (1), Trevon Cadogan (1), Warren Trotman (1) |
| 7 | Wednesday, 15th January 2020 | 3.30 pm | Deighton Griffith Secondary School | Alleyne School | 3:2 | DGSS: 11' Shamari Harewood, 68' Richem Atherley, 70+' OG ALL; ALL: Dandre Mitchell, Thierry Corbin |
| 7 | Wednesday, 15th January 2020 | 3.30 pm | Queen’s College | Alexandra School | 3:0* | * by forfeit |
| 7 | Tuesday, 25th February 2020 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | The Lodge School | 3:0* | * by forfeit |
| 8 | Friday, 24th January 2020 | 3.30 pm | The St. Michael School | Christ Church Foundation School | 3:2 | SMS: Jaquan Pilgrim (2), Joshua Collymore (1); CCFS: Jalen Johnson, Jelani Joseph |
| 8 | Friday, 24th January 2020 | 3.30 pm | Alleyne School | Combermere School | 1:3 | COM: Marcus Whittington, Ethan Taylor, Quashaun Lynch |
| 8 | Friday, 14th February 2020 | 3.30 pm | Alexandra School | Harrison College | 4:0 | AX: Antonio Skeete (1), Demario Francis (2), Rayna Cummins (1) |
| 8 | Friday, 31st January 2020 | 3.30 pm | The Lodge School | Deighton Griffith Secondary School | 3:2 | LOD: Shakeri Blades (2), Reuben Jacobs (1); DGSS: 20' Richem Atherley, 33' Teon Cadogan |
| 8 | rescheduled | | Pinehill St. Leonard’s Boys’ Secondary School | Queen’s College | | |
| 9 | Wednesday, 29th January 2020 | 3.30 pm | Christ Church Foundation School | Alleyne School | 5:0 | CCFS: Jalen Johnson (2), Daniel Thomas (1), Jayden Phillips (1), Thierry Gibson (1) |
| 9 | Friday, 31st January 2020 | 3.30 pm | The St. Michael School | Alexandra School | 2:2 | SMS: Zaccheo Quimby-Ward, OG AX); AX: Dontae Cumberbatch, Rayna Cummins |
| 9 | Wednesday, 29th January 2020 | 3.30 pm | Combermere School | The Lodge School | 1:0 | COM: Nathan Forde |
| 9 | Friday, 14th February 2020 | 3.30 pm | Harrison College | Pinehill St. Leonard’s Boys’ Secondary School | 0:7 | |
| 9 | Wednesday, 29th January 2020 | 3.30 pm | Deighton Griffith Secondary School | Queen’s College | 0:3 | QC: Kishmar Ramsey, Ethan Squires, Dominic Downes |
