| 2026-02-07 17:00:00February 7, 2026 | Arklow Town A vs St. Anthonys | 1 - 6 | Wicklow Cup | 2025/26 | Travers Insurance Park | Recap | - |
| 2026-02-26 19:45:00February 26, 2026 | Arklow United B vs Aughrim Rangers | 1 - 1 | Wicklow Cup | 2025/26 | Arklow Credit Union Park | Recap | - |
| 2026-02-28 14:30:00February 28, 2026 | Ashford Rovers B vs Shillelagh United | 3 - 0 | Wicklow Cup | 2025/26 | Ballinalea Park | Recap | - |
| 2026-02-28 15:00:00February 28, 2026 | Wicklow Rovers B vs Newtown United | 1 - 6 | Wicklow Cup | 2025/26 | Whitegates | Recap | - |
| 2026-03-01 11:00:00March 1, 2026 | Ballywaltrim B vs Roundwood | 1 - 2 | Wicklow Cup | 2025/26 | Ballywaltrim Community Centre | Recap | - |
| 2026-03-01 11:30:00March 1, 2026 | Carnew vs Coolboy Rangers | 7 - 1 | Wicklow Cup | 2025/26 | Back Alley | Recap | - |
| 2026-03-01 11:30:00March 1, 2026 | Wicklow Town vs Arklow United A | 4 - 2 | Wicklow Cup | 2025/26 | Finlay Park | Recap | - |
| 2026-03-01 14:00:00March 1, 2026 | Glencormac United A vs Ashford Rovers A | 2 - 1 | Wicklow Cup | 2025/26 | Ryder Field | Recap | - |
| 2026-04-24 19:45:00April 24, 2026 | Arklow United B vs Arklow Celtic | 3 - 0 | Wicklow Cup | 2025/26 | Arklow Credit Union Park | Recap | - |
| 2026-04-26 11:30:00April 26, 2026 | Roundwood vs Glencormac United A | 0 - 5 | Wicklow Cup | 2025/26 | Vartry Park | Recap | - |
| 2026-04-26 11:30:00April 26, 2026 | Newtown United vs Arklow Town B | 3 - 0 | Wicklow Cup | 2025/26 | Matt Kelly Community Grounds | Recap | - |
| 2026-04-26 11:30:00April 26, 2026 | Avonmore vs Ashford Rovers B | 1 - 2 | Wicklow Cup | 2025/26 | Ballygannon | Recap | - |
| 2026-04-26 14:00:00April 26, 2026 | Carnew vs Glencormac United B | 6 - 2 | Wicklow Cup | 2025/26 | Back Alley | Recap | - |
| 2026-04-26 14:00:00April 26, 2026 | Rathnew vs Ballywaltrim A | 4 - 2 | Wicklow Cup | 2025/26 | Shamrock Park | Recap | - |
| 2026-04-26 14:30:00April 26, 2026 | St. Anthonys vs Wicklow Rovers A | 5 - 1 | Wicklow Cup | 2025/26 | Finn Park | Recap | - |
| 2026-04-26 14:30:00April 26, 2026 | Wicklow Town vs St. Patricks | 5 - 1 | Wicklow Cup | 2025/26 | Finlay Park | Recap | - |
| 2026-05-16 14:00:00May 16, 2026 | Ashford Rovers B vs Carnew | 2 - 1 | Wicklow Cup | 2025/26 | Ballinalea Park | Recap | - |
| 2026-05-17 14:00:00May 17, 2026 | Rathnew vs Arklow United B | 11 - 0 | Wicklow Cup | 2025/26 | Shamrock Park | Recap | - |
| 2026-05-24 14:00:00May 24, 2026 | St. Anthonys vs Glencormac United A | 2 - 0 | Wicklow Cup | 2025/26 | Finn Park | Recap | - |
| 2026-05-27 18:45:00May 27, 2026 | Newtown United vs Wicklow Town | 2 - 2 | Wicklow Cup | 2025/26 | Matt Kelly Community Grounds | Recap | - |
| 2026-06-07 11:30:00June 7, 2026 | St. Anthonys vs Ashford Rovers B | 3 - 1 | Wicklow Cup | 2025/26 | Shamrock Park | Recap | - |
| 2026-06-07 11:30:00June 7, 2026 | Newtown United vs Rathnew | 0 - 4 | Wicklow Cup | 2025/26 | Finlay Park | Recap | - |
| 2026-06-21 15:00:00June 21, 2026 | St. Anthonys vs Rathnew | 1 - 2 | Wicklow Cup | 2025/26 | Kane Group Build Park | Recap | - |
