1. Round
10/08/2019 14:00 PSNI FC - Queen's University Belfast 3:1
15:00 Knockbreda FC - Ballyclare Comrades 1:7
15:00 Loughgall FC - Banbridge Town 2:1
15:00 Armagh City FC - HW Welders 0:6
2. Round
27/08/2019 19:45 Ballymena United - Newington Youth Club 3:0
19:45 Dundela FC - Tobermore United 6:0
19:45 Dungannon Swifts - Dergview FC 2:0
19:45 Portadown FC - Dollingstown FC 1:2
19:45 Limavady United - Ards FC 4:2
19:45 Warrenpoint Town - HW Welders 2:4
19:45 Bangor FC - Carrick Rangers 5:3 aet
19:45 Moyola Park FC - Cliftonville FC 1:3
19:45 Larne FC - Lisburn Distillery 3:0
19:45 Loughgall FC - Newry City FC 0:1
19:45 Coleraine FC - Annagh United 4:0
19:45 Glenavon FC - Portstewart FC 4:1
19:45 Glentoran Belfast - Ballyclare Comrades 4:1
19:45 Crusaders FC - Lurgan Celtic dnp
28/08/2019 19:45 Institute FC Drumahoe - PSNI FC 3:2
17/09/2019 20:00 Ballinamallard United FC - Linfield FC 4:5 aet
Round of 16
08/10/2019 19:45 Ballymena United - Dollingstown FC 6:0
19:45 Dungannon Swifts - Linfield FC 0:4
19:45 Coleraine FC - Glentoran Belfast 2:1
19:45 Institute FC Drumahoe - HW Welders 3:0
19:45 Larne FC - Dundela FC 1:3
19:45 Cliftonville FC - Bangor FC 3:2
19:45 Limavady United - Crusaders FC 1:4
23/10/2019 19:45 Glenavon FC - Newry City FC 2:3
Quarter-finals
29/10/2019 19:45 Ballymena United - Crusaders FC 1:2
19:45 Dundela FC - Coleraine FC 1:5
19:45 Newry City FC - Institute FC Drumahoe 0:1
19:45 Linfield FC - Cliftonville FC 1:0
Semi-finals
03/12/2019 19:45 Crusaders FC - Institute FC Drumahoe 2:0
19:45 Linfield FC - Coleraine FC 0:3
Final
15/02/2020 15:00 Crusaders FC - Coleraine FC -:-