| Shield quarter-finals | 1 | Friday, 30th June 2023 | 3.30 pm | Ellerslie Secondary School (TES) | Coleridge and Parry School (CP) | 5:0 | ELL: Jayden Atherley, Maleek Peters, Allego Yearwood, Zavani Best-Watkins, Daniel Matthews | |
| Shield quarter-finals | 2 | Friday, 30th June 2023 | 3.30 pm | St. George Secondary School (SGSS) | Parkinson Memorial Secondary School (PARK) | 2:0 | | |
| Shield quarter-finals | 3 | Friday, 30th June 2023 | 3.30 pm | Christ Church Foundation School (CCFS) | The Lester Vaughan School (LVS) | 3:0* | * by forfeit | |
| Shield quarter-finals | 4 | Friday, 30th June 2023 | 3.30 pm | Frederick Smith Secondary School (FSSS) | The St. Michael School (SMS) | 3:0* | * by forfeit | |
| Quarter-Finals | 5 | Monday, 19th June 2023 | 3.30 pm | St. Leonard’s Boys’ Secondary School (SLB) | Alleyne School (ALL) | 2:0 | SLB: Tyrique Collymore 20', Diego Phillips 35' | |
| Quarter-Finals | 6 | Wednesday, 28th June 2023 | 3.30 pm | Harrison College (HC) | Queen’s College (QC) | 1:3 | QC: Rasheed Hodge-Cave, Keigan Greenidge (PK), Zachary Lowe | |
| Quarter-Finals | 7 | Friday, 30th June 2023 | 3.30 pm | Deighton Griffith Secondary School (DGSS) | Grantley Adams Memorial School (GAMS) | 5:1 | DGSS: Élément Walcott 7', Zion Skeete 13', Jacobi Lovell 15', Élément Walcott 24', Élément Walcott 56' | |
| Quarter-Finals | 8 | Friday, 30th June 2023 | 3.30 pm | Combermere School (CS) | The Lodge School (LOD) | 0:1 | LOD: Adam King | |
| Shield Semi-Finals | 9 | Friday, 7th July 2023 | 1.45 pm | Christ Church Foundation School (CCFS) | Ellerslie Secondary School (TES) | 3:3 (1:3 PSO) | ELL: Maleek Peters (2), Daniel Matthews, PSO: Allego Yearwood, Jayden Atherley, Maleek Peters | |
| Shield Semi-Finals | 10 | Friday, 7th July 2023 | 3.00 pm | St. George Secondary School (SGSS) | Frederick Smith Secondary School (FSSS) | 3:0* | * by forfeit | |
| Semi-Finals | 11 | Friday, 7th July 2023 | 1.45 pm | St. Leonard’s Boys’ Secondary School (SLB) | Deighton Griffith Secondary School (DGSS) | 0:2 | DGSS: Arron Atherley 28’, Tyniko Bradshaw 49’ | |
| Semi-Finals | 12 | Friday, 7th July 2023 | 3.00 pm | The Lodge School (LOD) | Queen’s College (QC) | 3:3 (5:4 PSO) | LOD: Zach King, Tajiri Chase, Kevio Brathwaite | |
| Shield Final | 13 | Thursday, 13th July 2023 | 1.45 pm | Ellerslie Secondary School (TES) | St. George Secondary School (SGSS) | 2:0 | ELL: Maleek Peters, Jayden Atherley | |
| Final | 14 | Thursday, 13th July 2023 | 3.00 pm | Deighton Griffith Secondary School (DGSS) | The Lodge School (LOD) | 4:1 | DGSS: Arron Atherley, Jacobi Lovell (2), Élément Walcott (PK); LOD: Tye Waterman | |
