| 1 | Friday, 18th November 2022 | 3.30pm | Alleyne School | Ellerslie Secondary School | 1:0 | | |
| 1 | Monday, 31st October 2022 | 3.30pm | The Lester Vaughan School | Coleridge and Parry School | 0:2 | CP: Rojay Sobers 19', Kobe Williams 43' | |
| 1 | Monday, 31st October 2022 | 3.30pm | Queen’s College | Pinehill St. Leonard’s Boys’ Secondary School | 1:0 | QC: Jordan Bryan | |
| 1 | Monday, 31st October 2022 | 3.30pm | Frederick Smith Secondary School | Alexandra School | 1:10 | AX: Tashawn Nurse (3), Damario Francis (3), Myles Brewster, Aiden Vaughan, Azure Cumberbatch, Omar Harris | |
| 1 | Monday, 31st October 2022 | 3.30pm | Daryll Jordan Secondary School | Parkinson Memorial Secondary School | 1:3 | PARK: Nicholas Cox, Tyrico Bellamy, Blair Spencer | |
| 2 | Monday, 7th November 2022 | 3.30pm | Combermere School | The Lester Vaughan School | 2:2 | COM: Ethan Taylor, Erico Harris-Mullin: LVS: Disherid Franklyn Harewood, Tremon Francis | |
| 2 | Monday, 7th November 2022 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Alleyne School | 2:1 | SLB: Joshua Clarke, Devonte Clarke | |
| 2 | Monday, 7th November 2022 | 3.30pm | Coleridge and Parry School | Frederick Smith Secondary School | 5:1 | CP: Joshua Husbands 6' (P), Rojay Sobers 10', Kobe Williams 26', Kamari Johnson 36', Jayden Carter 62', yellow card Kamari Johnson; FSSS: Tre Demendonca 22' | |
| 2 | Monday, 7th November 2022 | 3.30pm | Parkinson Memorial Secondary School | Queen’s College | 1:1 | PARK: Tarel Rouse 33'; QC: Christopher Ward 72' | |
| 2 | Monday, 7th November 2022 | 3.30pm | Alexandra School | Daryll Jordan Secondary School | 1:0 | AX: Jamali Morgan | |
| 3 | Monday, 14th November 2022 | 3.30pm | Ellerslie Secondary School | Pinehill St. Leonard’s Boys’ Secondary School | 1:3 | ELL: Amari Layne; SLB: Joshua Yarde (2), Rivaldo Massiah | |
| 3 | Monday, 14th November 2022 | 3.30pm | Frederick Smith Secondary School | Combermere School | 1:1 | FSSS: Marcus Whittington; COM: Jean Luc Stoute | |
| 3 | Monday, 14th November 2022 | 3.30pm | Alleyne School | Parkinson Memorial Secondary School | 1:1 | ALL: Deondre Mitchell; PARK: Mikyle Norgrove | |
| 3 | Monday, 14th November 2022 | 3.30pm | Daryll Jordan Secondary School | Coleridge and Parry School | 2:2 | DJSS: Thierry Bradshaw (2); CP: Kamari Johnson 21', Giovanni Goodridge 59' | |
| 3 | Monday, 14th November 2022 | 3.30pm | Queen’s College | Alexandra School | 0:1 | AX: Tashawn Nurse | |
| 4 | Friday, 25th November 2022 | 3.30pm | The Lester Vaughan School | Frederick Smith Secondary School | 3:2 | LVS: Ke-mani Maynard (2), Tremon Francis: FSSS: Jadine Gilkes, Marcus Whittington | |
| 4 | Monday, 21st November 2022 | 3.30pm | Parkinson Memorial Secondary School | Ellerslie Secondary School | 6:1 | PARK: Kevin Webster 33', Mikyle Norgrove 2' & 55', Tyrese Thorne 18' & 20', Rashay Quintyne 81' (PK) | |
| 4 | Monday, 16th January 2023 | 3.30pm | Combermere School | Daryll Jordan Secondary School | 1:0 | COM: Quashaun Lynch | |
| 4 | Monday, 16th January 2023 | 3.30pm | Alexandra School | Alleyne School | 0:3* | * by forfeit | |
| 4 | Monday, 21st November 2022 | 3.30pm | Coleridge and Parry School | Queen’s College | 2:2 | CP: Joshua Husbands 14', Kobe Williams 44', red card: Tyjae Delpeache 69'; QC: Jordan Bryan (2); ELL: Amari Layne | |
| 5 | Monday, 28th November 2022 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Parkinson Memorial Secondary School | 5:1 | SLB: Joshua Yarde (2), Rivaldo Massiah (2), own goal; PARK: Shamar Blanchard | |
| 5 | Monday, 28th November 2022 | 3.30pm | Daryll Jordan Secondary School | The Lester Vaughan School | 2:3 | DJSS: Thierry Bradshaw 21' & 30'; LVS: Disherid Franklyn Harewood, Shakeem Johnson, Ke-mani Maynard | |
| 5 | Monday, 28th November 2022 | 3.30pm | Ellerslie Secondary School | Alexandra School | 0:4 | AX: Joshua Waithe (2), Damario Francis, Tashay Jones | |
| 5 | Monday, 27th February 2023 | 3.30pm | Queen’s College | Combermere School | 3:1 | QC: Thierry Ince, Ronan Lee (2); COM: James Arthur | |
| 5 | Monday, 28th November 2022 | 3.30pm | Alleyne School | Coleridge and Parry School | 0:3* | * by forfeit | |
| 6 | Monday, 5th December 2022 | 3.30pm | Daryll Jordan Secondary School | Frederick Smith Secondary School | 3:0* | * by forfeit | |
| 6 | Monday, 5th December 2022 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Alexandra School | 4:2 | SLB: Adriano Bascombe, Joshua Yarde, Rivaldo Massiah (2); AX: Myles Brewster, Tashay Jones; red card: Raheem Agard (AX) | |
| 6 | Monday, 5th December 2022 | 3.30pm | Queen’s College | The Lester Vaughan School | 4:3 | QC: Jordan Bryan, Thierry Ince (2), Dominic Downes; LVS: Tremon Francis, Disherid Franklyn Harewood, Nyzarie Bartlett | |
| 6 | Monday, 5th December 2022 | 3.30 pm | Ellerslie Secondary School | Coleridge and Parry School | 2:4 | ELL: Keenan Griffith, Amari Layne (PK); CP: Kamari Johnson 11', 16', 82', Joshua Husbands 18'; red card: Joshua Husbands (CP) | |
| 6 | Monday, 5th December 2022 | 3.30pm | Alleyne School | Combermere School | 2:1 | ALL: Keshaun King, Keary Barrow; COM: Quashaun Lynch | |
| 7 | Wednesday, 1st March 2023 | 3.30pm | Alexandra School | Parkinson Memorial Secondary School | 0:3* | * by forfeit | |
| 7 | Wednesday, 1st March 2023 | 3.30pm | Frederick Smith Secondary School | Queen’s College | 0:3* | * by forfeit | |
| 7 | Wednesday, 1st March 2023 | 3.30pm | Coleridge and Parry School | Pinehill St. Leonard’s Boys’ Secondary School | 2:2 | CP: Ahzari Dallaway, Kamari Johnson | |
| 7 | Wednesday, 1st March 2023 | 3.30pm | The Lester Vaughan School | Alleyne School | 0:1 | ALL: Keary Barrow | |
| 7 | Monday, 12th December 2022 | 3.30pm | Combermere School | Ellerslie Secondary School | 3:1 | COM: Ethan Taylor, Quashaun Lynch, Tariq Baker; ELL: Tre Moore | |
| 8 | Friday, 3rd March 2023 | 3.30pm | Queen’s College | Daryll Jordan Secondary School | 4:1 | QC: Ajani Headley, Caleb Williams, Jordan Bryan, Ronan Lee; DJSS: Thierry Bradshaw | |
| 8 | Monday, 20th March 2023 | 3.30pm | Parkinson Memorial Secondary School | Coleridge and Parry School | 1:2 | CP: Joshua Husbands (2) | |
| 8 | Friday, 3rd March 2023 | 3.30pm | Alleyne School | Frederick Smith Secondary School | 3:0* | * by forfeit | |
| 8 | Wednesday, 15th March 2023 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Combermere School | 3:1 | COM: Tariq Barker | |
| 8 | Friday, 3rd March 2023 | 3.30pm | Ellerslie Secondary School | The Lester Vaughan School | 1:1 | ELL: Shazek Scantlebury, LVS: Teon Jupiter | |
| 9 | Monday, 6th March 2023 | 3.30pm | Coleridge and Parry School | Alexandra School | 3:0* | * by forfeit | |
| 9 | Monday, 6th March 2023 | 3.30pm | Daryll Jordan Secondary School | Alleyne School | 1:1 | DJSS: Thierry Bradshaw; ALL: Deondre Mitchell | |
| 9 | Monday, 6th March 2023 | 3.30pm | Combermere School | Parkinson Memorial Secondary School | 4:1 | COM: Quashaun Lynch (2), James Arthur, Jean-Luc Stoute | |
| 9 | Monday, 20th March 2023 | 3.30pm | Frederick Smith Secondary School | Ellerslie Secondary School | 1:0 | | |
| 9 | Monday, 6th March 2023 | 3.30pm | The Lester Vaughan School | Pinehill St. Leonard’s Boys’ Secondary School | 2:2 | LVS: Jadyn Murray (2) | |
| 10 | Wednesday, 8th March 2023 | 3.30pm | Alleyne School | Queen’s College | 1:1 | ALL: Deondre Mitchell (PK); QC: Kiron Quimby | |
| 10 | Wednesday, 8th March 2023 | 3.30pm | Alexandra School | Combermere School | 0:3* | * by forfeit | |
| 10 | Wednesday, 22nd March 2023 | 3.30pm | Ellerslie Secondary School | Daryll Jordan Secondary School | 1:2 | ELL: Schzek Scantlebury; DJSS: Daymon Lyte, Tyric Halley | |
| 10 | Wednesday, 8th March 2023 | 3.30pm | Parkinson Memorial Secondary School | The Lester Vaughan School | 3:0* | * by forfeit | |
| 10 | Wednesday, 8th March 2023 | 3.30pm | Pinehill St. Leonard’s Boys’ Secondary School | Frederick Smith Secondary School | 3:2 | | |
| 11 | Monday, 13th March 2023 | 3.30pm | Combermere School | Coleridge and Parry School | 1:1 | COM: Ethan Taylor; CP: Roniko Harding | |
| 11 | Monday, 13th March 2023 | 3.30pm | Queen’s College | Ellerslie Secondary School | 5:2 | QC: Ronan Lee (2), Jordan Bryan, Dominic Downes, Thierry Ince; ELL: Amari Layne (PK), Schzek Scantleury | |
| 11 | Monday, 13th March 2023 | 3.30pm | The Lester Vaughan School | Alexandra School | 3:0* | * by forfeit | |
| 11 | Monday, 13th March 2023 | 3.30pm | Daryll Jordan Secondary School | Pinehill St. Leonard’s Boys’ Secondary School | 3:4 | DJSS: Jacobi Thompson (2), DaShawn Howell | |
| 11 | Friday, 17th March 2023 | 3.30pm | Frederick Smith Secondary School | Parkinson Memorial Secondary School | 1:3 | FSSS: Kemar Smith: PARK: Mikyle Norgrove (2), Shamari Greenidge-Lewis | |
