| Round 1Saturday 21st August | New Plymouth Mariners | 1–4 | Whitburn Carew | 1 |
| Round 2Saturday 28th August | Whitburn Carew | 2–1 | Adelaide Wanderers | 1 |
| Round 3Saturday 4th September | Hereford & Aspley | 0–1 | Whitburn Carew | 1 |
| Round 4Saturday 11th September | Whitburn Carew | 3–1 | Worthington Rovers | 1 |
| Round 5Saturday 18th September | Carmichael Town | 1–3 | Whitburn Carew | 1 |
| Round 6Saturday 25th September | Whitburn Carew | 3–0 | Real San Domingo | 1 |
| Round 7Saturday 2nd October | South Bay Sports | 0–4 | Whitburn Carew | 1 |
| Round 8Saturday 9th October | Whitburn Carew | 0–0 | Wincanton Athletic | 1 |
| Round 9Saturday 16th October | St Vincent All Stars | 1–3 | Whitburn Carew | 1 |
| Round 10Saturday 23rd October | Whitburn Carew | 6–0 | Baptist Railway Athletic | 1 |
| Round 11Saturday 30th October | Palmerston United | 3–1 | Whitburn Carew | 1 |
| Round 12Saturday 6th November | Whitburn Carew | 1–0 | Deportivo León | 1 |
| Round 13Saturday 20th November | Sancti Spiritus | 3–3 | Whitburn Carew | 1 |
| Round 14Saturday 27th November | Little Padstow | 2–4 | Whitburn Carew | 1 |
| Round 15Saturday 4th December | Whitburn Carew | 1–0 | Jessopstown Rangers | 1 |
| Round 16Saturday 11th December | Santiago de Brados | 2–3 | Whitburn Carew | 1 |
| Round 17Saturday 18th December | Whitburn Carew | 3–0 | Port Orient Battery | 1 |
| Round 18Sunday 26th December | Whitburn Carew | 1–0 | New Plymouth Mariners | 1 |
| Round 19Saturday 1st January | Adelaide Wanderers | 2–0 | Whitburn Carew | 1 |
| Round 20Saturday 15th January | Whitburn Carew | 4–3 | Hereford & Aspley | 1 |
| Round 21Saturday 22nd January | Worthington Rovers | 0–2 | Whitburn Carew | 1 |
| Round 22Saturday 5th February | Whitburn Carew | 1–1 | Carmichael Town | 1 |
| Round 23Saturday 12th February | Real San Domingo | 2–0 | Whitburn Carew | 1 |
| Round 24Saturday 19th February | Whitburn Carew | 1–0 | South Bay Sports | 1 |
| Round 25Saturday 26th February | Wincanton Athletic | 0–2 | Whitburn Carew | 1 |
| Round 26Saturday 12th March | Whitburn Carew | 1–2 | St Vincent All Stars | 2 |
| Round 27Saturday 19th March | Baptist Railway Athletic | 1–1 | Whitburn Carew | 2 |
| Round 28Saturday 26th March | Whitburn Carew | 1–0 | Palmerston United | 1 |
| Round 29Saturday 2nd April | Deportivo León | 0–2 | Whitburn Carew | 1 |
| Round 30Saturday 9th April | Whitburn Carew | 2–3 | Sancti Spiritus | 2 |
| Round 31Saturday 16th April | Whitburn Carew | 4–0 | Little Padstow | 2 |
| Round 32Saturday 23rd April | Jessopstown Rangers | 0–0 | Whitburn Carew | 2 |
| Round 33Saturday 30th April | Whitburn Carew | 2–0 | Santiago de Brados | 2 |
| Round 34Saturday 7th May | Port Orient Battery | 1–3 | Whitburn Carew | 2 |
| Play-off Semi-final, first legSunday 15th May | St Vincent All Stars | 0–2 | Whitburn Carew | |
| Play-off Semi-final, second legThursday 19th May | Whitburn Carew | 2–2 | St Vincent All Stars | |
| Play-off FinalSaturday 28th May | Whitburn Carew | 3–3 | Sancti Spiritus | |