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| ROUND | GAME | DATE | KICK-OFF | HOME | AWAY | RESULT | SCORERS |
|---|---|---|---|---|---|---|---|
| Quarter-Finals | 1 | Monday, 20th February 2023 | 3.30 pm | Combermere School | The Lodge School | 4:0 | COM: Radarico Marques (3), Amari Small |
| Quarter-Finals | 2 | Wednesday, 22nd February 2023 | 3.30 pm | Pinehill St. Leonard’s Boys’ Secondary School | Princess Margaret Secondary School | 6:0 | SMS: Jordan Blackman, Alec Welch, Ethan McCollin, LVS: Tremon Francis |
| Quarter-Finals | 3 | Wednesday, 22nd February 2023 | 3.30 pm | The St. Michael School | The Lester Vaughan School | 3:1 | SMS: Jordan Blackman, Alec Welch, Ethan McCollin, LVS: Tremon Francis |
| Quarter-Finals | 4 | Friday, 24th February 2023 | 3.30 pm | Deighton Griffith Secondary School | Alleyne School | 4:4 (4:3 PSO) | DGSS: 16' Arron Atherley, 24' Élément Walcott, 55' Élément Walcott, 70'+1' Arron Atherley |
| Semi-Finals | 5 | Monday, 3rd April 2023 | 3.30 pm | Combermere School | Pinehill St. Leonard’s Boys’ Secondary School | 0:2 | SLB: Semaj Best, Oshai Mayers |
| Semi-Finals | 6 | Tuesday, 4th April 2023 | 3.30 pm | The St. Michael School | Deighton Griffith Secondary School | 3:0 | SMS: Jamarco Johnson (2), Ari Manning |
| Final | 7 | Thursday, 6th April 2023 | 5.00pm | Pinehill St. Leonard’s Boys’ Secondary School | The St. Michael School | 2:1 | SLB: Jamarrio Yarde 47', Reuben Garnes Alleyne 54'; SMS: Ari Manning (pk) 63' |
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