Saturday, 7th May, 2011 Final

• Crusaders 1-2 Linfield (at Windsor Park)

Saturday, 9th April, 2011 Semi-finals

• Crusaders 3-1 Portadown (at Mourneview Park)
• Glentoran 0-2 Linfield (at Windsor Park)

Monday, 14th March, 2011 Quarter-final Replays

• Coleraine 3-3 (2-3p) Glentoran
• Glenavon 0-3 Portadown

Saturday, 5th March, 2011 Quarter-finals

• Ballinamallard United 0-5 Crusaders
• Dungannon Swifts 0-2 Linfield
• Glentoran 1-1 Coleraine
• Portadown 3-3 Glenavon

Monday, 21st February, 2011 Sixth Round Replays

• Ballinamallard United 4-2 Lisburn Distillery
• Linfield 3-0 Dunmurry Rec.
• Portadown 1-0 HW Welders

Saturday, 12th February, 2011 Sixth Round

• Carrick Rangers 1-3 Coleraine
• Crusaders 2-1 Nortel
• Dungannon Swifts 4-2 Warrenpoint Town
• Glenavon 2-0 Queen's University
• Glentoran 3-1 Loughgall
• HW Welders 1-1 Portadown
• Linfield 1-1 Dunmurry Rec.
• Lisburn Distillery 2-2 Ballinamallard United

Tuesday 1st February, 2011 Fifth Round Replay

• Ards 0-1 HW Welders

Wednesday 26th January, 2011 Fifth Round Replay

• Carrick Rangers 6-1 Shankill United

Tuesday 25th January, 2011 Fifth Round

• Ards 2-2 HW Welders
• Limavady United 1-2 Coleraine

Tuesday 25th January, 2011 Fifth Round Replays

• Cliftonville 0-0 (1-3p) Warrenpoint Town
• Glentoran 3-2 Ballymena United
• Kilmore Rec. 0-5 Dunmurry Rec.

Saturday 15th January 2011 Fifth Round

• Albert Foundry 0-2 Nortel
• Annagh United 2-6 Glenavon
• Ballinamallard United 3-1 Larne
• Ballymena United 1-1 Glentoran
• Carrick Rangers 3-3 Shankill United
• Crusaders 3-2 Newry City
• Dundela 1-4 Lisburn Distillery
• Dungannon Swifts 5-1 Ballymoney United
• Dunmurry Rec. 2-2 Kilmore Rec.
• Linfield 5-1 Institute
• Loughgall 3-1 Sport & Leisure Swifts
• Portadown 4-3 Donegal Celtic
• Queen's University 1-0 Crumlin United
• Warrenpoint Town 1-1 Cliftonville

Saturday 15th January 2011 Fourth Round

• Coagh United 2-5 Ards
• Limavady United 2-0 Wakehurst

Monday 3rd January 2011 Fourth Round

• Glebe Rangers 1-2 Nortel

Saturday 11th December 2010 Fourth Round

• Albert Foundry 3-1 Rosario YC
• Annagh United 2-1 Killymoon Rangers
• Armagh City 2-3 Crumlin United
• Ballyclare Comrades 2-4 HW Welders
• Banbridge Town 0-1 Shankill United
• Coagh United 1-3 Ards (score to remain on the records but the match is to be replayed by order of Challenge Cup Committee) 
• Dergview 2-3 Ballinamallard United
• Dundela 5-0 Chimney Corner
• Institute 0-0 (5-4p) Newington YC
• Knockbreda 0-2 Ballymoney United
• Larne 2-1 Bangor
• Lurgan Celtic 2-2 (4-5p) Dunmurry Rec.
• Moyola Park 1-6 Carrick Rangers
• Portstewart 0-2 Kilmore Rec.
• Queen's University 3-2 PSNI
• Sport & Leisure Swifts 5-3 Dungiven
• Tobermore United 3-5 Loughgall
• Warrenpoint Town 3-2 Comber Rec.

Saturday 27th November 2010 Third Round

• Ardglass 1-2 Kilmore Rec.

Saturday 20th November 2010 Third Round

• Ardstraw 3-6 Albert Foundry
• Broomhedge 0-5 Dunmurry Rec.
• Dollingstown 2-4 Comber Rec.
• Islandmagee 1-3 Dungiven
• Magherafelt Sky Blues 0-1 Shankill United
• Malachians 1-2 Crumlin United
• Newington YC 8-0 Tandragee Rovers
• Nortel 2-0 Camlough Rovers
• Rosario YC 3-1 Dromara Village

Saturday 23rd October 2010 Second Round

• Albert Foundry 3-1 Larne Tech. OB
• Ardglass 4-1 Bangor Swifts
• Ardstraw 2-1 Crewe United
• Ballynure OB 0-0 (4-5p) Broomhedge
• Brantwood 0-1 Dunmurry Rec.
• Camlough Rovers 2-0 Barn United
• Crumlin United 4-1 Bloomfield
• Derriaghy CC 2-3 Newington YC
• Dollingstown 5-3 Lisburn Rangers
• Downpatrick 0-4 Nortel
• Dromara Village 3-1 Downshire YM
• Dungiven 3-2 Newington Rangers
• Grove United 1-3 Comber Rec.
• Islandmagee 3-2 Abbey Villa
• Kilbride Swifts 2-3 Tandragee Rovers
• Kilmore Rec. 4-2 Killyleagh YC
• Magherafelt Sky Blues 2-0 Bryansburn Rangers
• Malachians 4-2 Ards Rangers
• Richhill 0-3 Shankill United
• Rosario YC 3-2 Wellington Rec.

Saturday 18th September 2010 First Round

• 18th Newtownabbey 2-5 Broomhedge 
• Abbey Villa 2-0 Ballynahinch United 
• AFC Craigavon 1-2 Shankill United 
• Ardglass 3-1 Sirocco Works 
• Ards Rangers 9-2 FC Ballynure 
• Ardstraw 6-1 Seagoe 
• Barn United 3-2 Saintfield United 
• Bloomfield 5-2 Hanover 
• Bryansburn Rangers 5-2 NFC Kesh 
• Camlough Rovers 5-2 Lurgan Town Boys 
• Desertmartin 0-2 Brantwood 
• Downpatrick 2-1 Drumaness Mills 
• Downshire YM 2-1 Holywood 
• Draperstown Celtic 1-2 Crewe United 
• Dromara Village 7-3 Lisanally Rangers 
• East Belfast 1-2 Newington Rangers 
• Fivemiletown United 2-6 Nortel 
• Islandmagee 4-1 Rathfern Rangers 
• Kilbride Swifts 4-3 Groomsport 
• Killyleagh YC 3-1 Banbridge Rangers 
• Kilmore Rec. 6-3 1st Bangor 
• Lisburn Rangers 6-1 Donard Hospital 
• Lower Maze 1-4 Grove United 
• Malachians 5-1 Bangor Rangers 
• Mossley YM 0-1 Crumlin United 
• Mountjoy United 1-2 Magherafelt Sky Blues 
• Newcastle 1-5 Dollingstown 
• Raceview 2-4 Comber Rec. 
• Rathfriland Rangers 1-2 Tandragee Rovers 
• Rosario YC 3-2 Laurelvale 
• Shorts 2-4 Ballynure OB 
• UUC withdrawn Albert Foundry walkover
• Wellington Rec. 5-0 Strabane