| 1 | 1 | Wednesday, 20th November 2019 | 3.30 pm | Combermere School | Princess Margaret Secondary School | 3:0 | |
| 1 | 2 | Wednesday, 20th November 2019 | 3.30 pm | Harrison College | St. George Secondary School | 4:0 | HC: Ethan Goodridge (3), Christian Collymore (1) |
| 1 | 3 | Wednesday, 20th November 2019 | 3.30 pm | Christ Church Foundation School | Parkinson Memorial Secondary School | 3:2 | CCFS: Jalen Johnson, Jayden Phillips, Thierry Gibson |
| 1 | 4 | Wednesday, 20th November 2019 | 3.30 pm | Daryll Jordan Secondary School | Deighton Griffith Secondary School | 0:3* | * by forfeit |
| 1 | 5 | Wednesday, 20th November 2019 | 3.30 pm | Alexandra School | St. Francis Secondary School | 0:3 | SFSS: Lee Blades (2), Zion Mayers (1) |
| 2 | 6 | Wednesday, 4th December 2019 | 3.30 pm | Graydon Sealy Secondary School | Combermere School | 1:5 | COM: Marcus Whittington (2), Ethan Taylor (1), Azari Brewster (1), Quashaun Lynch (1) |
| 2 | 7 | Wednesday, 20th November 2019 | 3.30 pm | The St. Michael School | Pinehill St. Leonard’s Boys’ Secondary School | 3:4 | SMS: Jaquan Pilgrim (3) |
| 2 | 8 | Wednesday, 4th December 2019 | 3.30 pm | Coleridge and Parry School | Harrison College | 5:0 | CP: Rovaldo Massiah (2), Tavian Eastmond (2), Najae Hinds (1) |
| 2 | 9 | Friday, 22nd November 2019 | 3.30 pm | Grantley Adams Memorial School | Christ Church Foundation School | 1:1 (3:4 by PSO) | GAMS: Jatario Precod; CCFS: Jayden Phillips |
| 2 | 10 | Tuesday, 4th February 2020 | 3.30 pm | Queen’s College | Deighton Griffith Secondary School | 3:1 | QC: Yanni Marshall, Na?f Lynch, Ethan Squires; DGSS: 33' Shamari Harewood |
| 2 | 11 | Wednesday, 5th February 2020 | 3.30 pm | Frederick Smith Secondary School | The Lester Vaughan School | 1:4 | LVS: Ke-mani Maynard (2), Jayden Mayers (2) |
| 2 | 12 | Friday, 22nd November 2019 | 3.30 pm | Alleyne School | St. Francis Secondary School | 0:6 | SFSS: Khaliq Haynes (3), Jahim Adams (2), Lee Blades (1) |
| 2 | 13 | Wednesday, 20th November 2019 | 3.30 pm | The Lodge School | Ellerslie Secondary School | 5:0 | LOD: Shakeri Blades (3), Seth Jervier (1), Jari Cummings (1) |
| Quarter-Finals | 14 | Wednesday, 5th February 2020 | 3.30 pm | Combermere School | Pinehill St. Leonard’s Boys’ Secondary School | 2:5 | |
| Quarter-Finals | 15 | Monday, 17th February 2020 | 3.30 pm | Coleridge and Parry School | Christ Church Foundation School | 0:2 | CCFS: Jayden Phillips, Jalen Johnson (PK) |
| Quarter-Finals | 16 | Monday, 17th February 2020 | 3.30 pm | Queen’s College | The Lester Vaughan School | 3:0 | QC: Kishmar Ramsey, Dominic Downes, Diego Fenty |
| Quarter-Finals | 17 | Wednesday, 5th February 2020 | 3.30 pm | St. Francis Secondary School | The Lodge School | 1:0 | |
| Semi-Finals | 18 | Friday, 21st February 2020 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Christ Church Foundation School | 3:3 (4:5 by PSO) | CCFS: Kenrian Harris, Jayden Phillips |
| Semi-Finals | 19 | Friday, 21st February 2020 | 3.30 pm | Queen’s College | St. Francis Secondary School | 3:0 | QC: Khalil Vanderpool-Nurse, Thierry Ince, Ethan Squires |
| 3rd place | 20 | Wednesday, 4th March 2020 | 2.00 pm | Pinehill St. Leonard’s Boys’ Secondary School | St. Francis Secondary School | 2:3 | SFSS: Kyle Corbin (1), Michael Walker (2) |
| Final | 21 | Wednesday, 4th March 2020 | 3.30 pm | Christ Church Foundation School | Queen’s College | 0:8 | QC: 1' Ethan Squires (0:1), 32' Khalil Vanderpool-Nurse (0:2), 35' Ethan Squires (0:3), 42' Khalil Vanderpool-Nurse (0:4) 43' Ethan Squires (0:5), 64' Dominic Small (0:6), 66' Justin Griffith (0:7), 70' Jordan Bryan (0:8) |
