Season Round date Home Result Guest
2021/2022 1. Round 18/09/2021 Coldstream FC Coldstream FC 1:10 East Kilbride FC East Kilbride FC
2011/2012 3. Round 19/11/2011 Airdrie United FC Airdrie United FC 11:0 Gala Fairydean Rovers Gala Fairydean Rovers
2023/2024 1. Round 23/09/2023 Gala Fairydean Rovers Gala Fairydean Rovers 8:2 Strathspey Thistle FC Strathspey Thistle FC
2016/2017 1. Round 24/09/2016 East Kilbride FC East Kilbride FC 9:1 Vale of Leithen FC Vale of Leithen FC
2011/2012 1. Round 24/09/2011 Wick Academy FC Wick Academy FC 9:1 Coldstream FC Coldstream FC
2008/2009 1. Round 27/09/2008 Banks O’ Dee FC Banks O’ Dee FC 10:0 Fort William FC Fort William FC
2023/2024 3. Round 25/11/2023 Annan Athletic Annan Athletic 4:5 aet Dumbarton FC Dumbarton FC
2017/2018 2. Round 14/10/2017 Peterhead FC Peterhead FC 9:0 Colville Park Colville Park
2016/2017 4. Round 21/01/2017 Bonnyrigg Rose Athletic Bonnyrigg Rose Athletic 1:8 Hibernian FC Hibernian FC
2016/2017 3. Round 26/11/2016 Elgin City Elgin City 8:1 Hawick Royal Albert Hawick Royal Albert
2016/2017 2. Round 29/10/2016 Formartine United Formartine United 7:2 Banks O’ Dee FC Banks O’ Dee FC
2014/2015 3. Round 08/11/2014 Bo'ness United Bo'ness United 5:4 Elgin City Elgin City
2014/2015 1. Round 13/09/2014 Cove Rangers Cove Rangers 9:0 Hawick Royal Albert Hawick Royal Albert
2013/2014 1. Round 14/09/2013 Forres Mechanics FC Forres Mechanics FC 4:5 Keith FC Keith FC
2012/2013 3. Round 03/11/2012 Cowdenbeath FC Cowdenbeath FC 8:1 Vale of Leithen FC Vale of Leithen FC
2011/2012 2. Round 22/10/2011 Auchinleck Talbot Auchinleck Talbot 8:1 Threave Rovers Threave Rovers
2011/2012 2. Round 22/10/2011 Wigtown & Bladnoch Wigtown & Bladnoch 0:9 Stranraer FC Stranraer FC
2011/2012 1. Round 01/10/2011 Irvine Meadow XI Irvine Meadow XI 6:3 Forres Mechanics FC Forres Mechanics FC
2011/2012 1. Round 24/09/2011 Gala Fairydean Rovers Gala Fairydean Rovers 8:1 Hawick Royal Albert Hawick Royal Albert
2010/2011 2. Round 23/10/2010 Stranraer FC Stranraer FC 9:0 St. Cuthbert Wanderers St. Cuthbert Wanderers
2009/2010 Round of 16 06/02/2010 Ross County FC Ross County FC 9:0 Stirling Albion FC Stirling Albion FC
2008/2009 1. Round 27/09/2008 Fraserburgh FC Fraserburgh FC 6:3 Hawick Royal Albert Hawick Royal Albert
2006/2007 3. Round 06/01/2007 Deveronvale FC Deveronvale FC 5:4 Elgin City Elgin City
2005/2006 1. Round 25/11/2005 Alloa Athletic Alloa Athletic 9:0 Selkirk FC Selkirk FC
1997/1998 3. Round 23/02/1998 Dunfermline Athletic Dunfermline Athletic 7:2 Edinburgh City FC Edinburgh City FC
1997/1998 3. Round 23/02/1998 Inverness CT Inverness CT 8:1 Annan Athletic Annan Athletic
2023/2024 1. Round 23/09/2023 East Kilbride FC East Kilbride FC 8:0 Whitehill Welfare Whitehill Welfare
2022/2023 3. Round 26/11/2022 Dundee FC Dundee FC 6:2 aet Airdrieonians FC Airdrieonians FC
2022/2023 2. Round 22/10/2022 Dalbeattie Star Dalbeattie Star 1:7 Darvel FC Darvel FC
2022/2023 1. Round 17/09/2022 Darvel FC Darvel FC 8:0 Tynecastle FC Tynecastle FC
2021/2022 1. Round 18/09/2021 Wigtown & Bladnoch Wigtown & Bladnoch 0:8 St. Cuthbert Wanderers St. Cuthbert Wanderers
2020/2021 2. Round 23/03/2021 Nairn County FC Nairn County FC 1:7 Montrose FC Montrose FC
2019/2020 Round of 16 18/02/2020 Motherwell FC Motherwell FC 4:4 St. Mirren FC St. Mirren FC
2017/2018 3. Round 18/11/2017 Banks O’ Dee FC Banks O’ Dee FC 2:6 Ayr United Ayr United
2017/2018 3. Round 18/11/2017 Lothian Thistle HV Lothian Thistle HV 1:7 St. Mirren FC St. Mirren FC
2017/2018 2. Round 14/10/2017 Stirling Albion FC Stirling Albion FC 3:5 Lothian Thistle HV Lothian Thistle HV
2017/2018 2. Round 14/10/2017 Buckie Thistle Buckie Thistle 6:2 BSC Glasgow BSC Glasgow
2017/2018 1. Round 23/09/2017 Clachnacuddin FC Clachnacuddin FC 8:0 Fort William FC Fort William FC
2016/2017 4. Round 21/01/2017 Ross County FC Ross County FC 6:2 Dundee United Dundee United
2016/2017 3. Round 26/11/2016 Buckie Thistle Buckie Thistle 3:5 Dunfermline Athletic Dunfermline Athletic
2016/2017 2. Round 29/10/2016 Gretna FC Gretna FC 2:6 Buckie Thistle Buckie Thistle
2016/2017 1. Round 01/10/2016 Hawick Royal Albert Hawick Royal Albert 6:2 Civil Service Strollers Civil Service Strollers
2015/2016 3. Round 28/11/2015 Inverurie Loco Works Inverurie Loco Works 4:4 Annan Athletic Annan Athletic
2014/2015 3. Round 01/11/2014 Elgin City Elgin City 4:4 Bo'ness United Bo'ness United
2014/2015 2. Round 04/10/2014 Bo'ness United Bo'ness United 7:1 Culter FC Culter FC
2014/2015 1. Round 13/09/2014 Clachnacuddin FC Clachnacuddin FC 1:7 Hurlford United Hurlford United
2013/2014 3. Round 02/11/2013 Elgin City Elgin City 3:5 Dunfermline Athletic Dunfermline Athletic
2013/2014 2. Round 05/10/2013 Edinburgh City FC Edinburgh City FC 4:4 Fraserburgh FC Fraserburgh FC
2012/2013 2. Round 29/09/2012 Cove Rangers Cove Rangers 8:0 Golspie Sutherland Golspie Sutherland
2011/2012 4. Round 07/01/2012 Airdrie United FC Airdrie United FC 2:6 Dundee United Dundee United