Anguilla Football League
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Holywood FC
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Clearer Water Irish Cup 2026/2027
Clearer Water Irish Cup 2025/2026
Clearer Water Irish Cup 2023/2024
Samuel Gelston’s Whiskey Irish Cup 2022/2023
Tennent's Irish Cup 2019/2020
2022-09-17
Holywood FC
Holywood FC
1 : 3
Crewe United FC
Crewe United
L
2023-08-12
Holywood FC
Holywood FC
1 : 2
Crumlin United FC
Crumlin Utd
L
2025-08-09
Holywood FC
Holywood FC
3 : 1
Banbridge Town FC
Banbridge
W
2025-09-12
Crumlin Star FC
Crumlin Star
1 : 2
Holywood FC
Holywood FC
W
2025-10-25
Holywood FC
Holywood FC
3 : 5
Finaghy FC
Finaghy
L
2026-08-08
Portaferry Rovers FC
Portaferry Rov
0 : 2
Holywood FC
Holywood FC
W
