Round 1
Saturday 20th August | Santiago de Brados | 1–5 | Jessopstown Rangers | 1 |
Round 2
Saturday 27th August | Jessopstown Rangers | 1–1 | Wincanton Athletic | 4 |
Round 3
Saturday 3rd September | Adelaide Wanderers | 2–0 | Jessopstown Rangers | 7 |
Round 4
Saturday 10th September | Jessopstown Rangers | 3–2 | Carmichael Town | 6 |
Round 5
Saturday 17th September | Little Padstow | 0–1 | Jessopstown Rangers | 4 |
Round 6
Saturday 24th September | Jessopstown Rangers | 2–1 | Carlton Town | 3 |
Round 7
Saturday 1st October | Edwalton | 0–2 | Jessopstown Rangers | 3 |
Round 8
Saturday 8th October | Jessopstown Rangers | 2–1 | AFC Droy | 3 |
Round 9
Saturday 15th October | Deportivo León | 0–1 | Jessopstown Rangers | 3 |
Round 10
Saturday 22nd October | Jessopstown Rangers | 1–0 | St Vincent All Stars | 3 |
Round 11
Saturday 29th October | Georgetown Atlantic | 2–0 | Jessopstown Rangers | 3 |
Round 12
Saturday 5th November | Jessopstown Rangers | 0–0 | Gresdon Methodists | 3 |
Round 13
Saturday 12th November | Bricknell Town | 1–1 | Jessopstown Rangers | 5 |
Round 14
Saturday 26th November | Port Orient Battery | 1–0 | Jessopstown Rangers | 5 |
Round 15
Saturday 3rd December | Jessopstown Rangers | 5–2 | Baptist Railway Athletic | 4 |
Round 16
Saturday 10th December | Palmerston United | 3–2 | Jessopstown Rangers | 5 |
Round 17
Saturday 17th December | Jessopstown Rangers | 1–0 | Sancti Spiritus | 4 |
Round 18
Saturday 31st December | Jessopstown Rangers | 2–1 | Santiago de Brados | 4 |
Round 19
Saturday 14th January | Wincanton Athletic | 0–3 | Jessopstown Rangers | 4 |
Round 20
Saturday 21st January | Jessopstown Rangers | 2–1 | Adelaide Wanderers | 4 |
Round 21
Saturday 4th February | Carmichael Town | 0–0 | Jessopstown Rangers | 4 |
Round 22
Saturday 11th February | Jessopstown Rangers | 1–1 | Little Padstow | 3 |
Round 23
Saturday 25th February | Carlton Town | 1–1 | Jessopstown Rangers | 3 |
Round 24
Saturday 4th March | Jessopstown Rangers | 3–0 | Edwalton | 3 |
Round 25
Saturday 11th March | AFC Droy | 3–1 | Jessopstown Rangers | 4 |
Round 26
Saturday 18th March | Jessopstown Rangers | 4–1 | Deportivo León | 4 |
Round 27
Saturday 25th March | St Vincent All Stars | 2–1 | Jessopstown Rangers | 4 |
Round 28
Saturday 1st April | Jessopstown Rangers | 0–1 | Georgetown Atlantic | 4 |
Round 29
Saturday 8th April | Gresdon Methodists | 1–2 | Jessopstown Rangers | 4 |
Round 30
Saturday 15th April | Jessopstown Rangers | 0–0 | Bricknell Town | 4 |
Round 31
Saturday 22nd April | Jessopstown Rangers | 2–2 | Port Orient Battery | 4 |
Round 32
Saturday 29th April | Baptist Railway Athletic | 0–0 | Jessopstown Rangers | 5 |
Round 33
Saturday 6th May | Jessopstown Rangers | 1–0 | Palmerston United | 5 |
Round 34
Sunday 14th May | Sancti Spiritus | 2–2 | Jessopstown Rangers | 4 |