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