Saturday, 1st November, 2008First Round
- Abbey Villa v. Newbuildings United
- Albert Foundry v. Portglenone
- Ards v. Queens University
- Armagh City v. Banbridge AFC
- Ballinamallard United v. Markethill Swifts
- Ballynahinch United v. Drumaness Mills
- Ballynure OB v. Wellington Rec.
- Bangor Reserves v. Loughgall
- Barn United v. Killymoon Rangers
- Blackers Mill v. Oxford United
- Bourneview YM v. Ballymoney United
- Brantwood v. Churchill United
- Bryansburn Rangers v. Ballymacash Rangers
- Comber Rec. v. Camlough Rovers
- Cookstown Athletic v. Lurgan Celtic
- Cookstown Olympic v. Coleraine Reserves
- Crewe United v. Annagh United
- Crumlin United v. Ballymena United Reserves
- Crusaders Reserves v. Malachians
- Dollingstown v. Roe Valley
- Downshire YM v. Dungiven
- Dunaghy v. Knockbreda
- Dundela v. Newcastle
- Dunmurry YM v. Lisanally Rangers
- East Belfast v. Sirocco Works
- Fivemiletown United v. 1st Bangor
- Glentoran II v. Desertmartin
- Grove United v. Larne
- Holywood v. Bloomfield
- Islandmagee v. Sport & Leisure
- Kilmore Rec. v. Coagh United
- Linfield Swifts v. AFC Craigavon
- Lisburn Rangers v. Dunmurry Rec.
- Lower Maze v. Strabane
- Lurgan Town Boys v. Limavady United
- Magherafelt Sky Blues v. Donard Hospital
- Mosside v. Wakehurst
- Newington YC v. Tandragee Rovers
- Newry City Reserves v. HW Welders
- Nortel v. Portadown
- Oxford United Stars v. Ballyclare Comrades
- Portadown BBOB v. Glebe Rangers
- PSNI v. UUC
- Rasharkin United v. Saintfield United
- Rosario YC v. Dergview
- Seagoe v. Chimney Corner
- Tobermore United v. Raceview
Byes: Ards Rangers, Banbridge Town, Broomhedge, Carrick Rangers, Donegal Celtic, Downpatrick, Draperstown Celtic, Dromara Village, Dundonald, Hanover, Killyleagh YC, Laurelvale, Moyola Park, Portstewart, Rathfern Rangers, Rathfriland Rangers, Warrenpoint Town
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