| 29 May 2011 | First Round | Falkland v Fauldhouse Victoria | Scroggie Park, Falkland | Results |
| 29 May 2011 | First Round | Holy Cross Academicals v Irvine | Arboretum, Edinburgh | Results |
| 29 May 2011 | First Round | Largo v Dundee High School Former Pupils | East Drive, Upper Largo | Results |
| 29 May 2011 | First Round | Hillhead High School Former Pupils v Stenhousemuir | Hughenden, Glasgow | Results |
| 29 May 2011 | First Round | Glasgow Academicals v Kelso | New Anniesland, Glasgow | Results |
| 29 May 2011 | First Round | Gala v Edinburgh Academicals | Meigle Park, Galashiels | Results |
| 29 May 2011 | First Round | St Boswells v Ferguslie | The Green, St Boswells | Results |
| 29 May 2011 | First Round | Huntly v East Kilbride | Castle Park, Huntly | Results |
| 29 May 2011 | First Round | Bon Accord v Highland | Aberdeen Links, Aberdeen | Results |
| 29 May 2011 | First Round | Dumfries v Renfrew | Nunholm, Dumfries | Results |
| 29 May 2011 | First Round | Edinburgh v Royal High Corstorphine | Grange Loan, Edinburgh | Results |
| 08 May 2011 | First Round | Kelburne v Freuchie | Whitehaugh Oval, Paisley | Results |
| 08 May 2011 | First Round | Penicuik v Weirs | Kirkhill, Penicuik | Results |
| 29 May 2011 | First Round | Poloc v Prestwick | Shawholm, Glasgow | Results |
| 07 May 2011 | First Round | Stewart's Melville Royal High v Boroughmuir | Inverleith, Edinburgh | Results |
| 29 May 2011 | First Round | West Lothian v Strathearn | Boghall, Linlithgow | Results |
| 05 Jun 2011 | Second Round | Greenock v West of Scotland | Glenpark, Greenock | Results |
| 05 Jun 2011 | Second Round | Kelburne v Holy Cross Academicals | Whitehaugh Oval, Paisley | Results |
| 05 Jun 2011 | Second Round | Carlton v Renfrew | Grange Loan, Edinburgh | Results |
| 05 Jun 2011 | Second Round | Stewart's Melville Royal High v Uddingston | Inverleith, Edinburgh | Results |
| 05 Jun 2011 | Second Round | Clydesdale v Drumpellier | Titwood, Glasgow | Results |
| 05 Jun 2011 | Second Round | Stirling County v Stenhousemuir | New Williamfield, Stirling | Results |
| 05 Jun 2011 | Second Round | East Kilbride v Forfarshire | Torrance House, East Kilbride | Results |
| 05 Jun 2011 | Second Round | Stoneywood-Dyce v Watsonians | People's Park, Aberdeen | Results |
| 05 Jun 2011 | Second Round | Ayr v West Lothian | Cambusdoon New Ground, Alloway | Results |
| 05 Jun 2011 | Second Round | Falkland v Glasgow Academicals | Scroggie Park, Falkland | Results |
| 05 Jun 2011 | Second Round | Dunfermline v Royal High Corstorphine | McKane Park, Dunfermline | Results |
| 05 Jun 2011 | Second Round | Dundee High School Former Pupils v Ferguslie | Forthill, Dundee | Results |
| 05 Jun 2011 | Second Round | Grange v Bon Accord | Raeburn Place, Edinburgh | Results |
| 05 Jun 2011 | Second Round | Arbroath United v Heriot's | Lochlands Park, Arbroath | Results |
| 05 Jun 2011 | Second Round | Edinburgh Academicals v Poloc | Edinburgh Academicals Ground, Raeburn Place, Edinburgh | Results |
| 05 Jun 2011 | Second Round | Aberdeenshire v Penicuik | Mannofield Park, Aberdeen | Results |
| 19 Jun 2011 | Third Round | East Kilbride v Arbroath United | Torrance House, East Kilbride | Results |
| 19 Jun 2011 | Third Round | Greenock v Clydesdale | Glenpark, Greenock | Results |
| 29 Jun 2011 | Third Round | Ferguslie v Kelburne | Meikleriggs, Paisley | Results |
| 19 Jun 2011 | Third Round | Carlton v Ayr | Grange Loan, Edinburgh | Results |
| 19 Jun 2011 | Third Round | Falkland v Uddingston | Scroggie Park, Falkland | Results |
| 19 Jun 2011 | Third Round | Dunfermline v Grange | McKane Park, Dunfermline | Results |
| 19 Jun 2011 | Third Round | Aberdeenshire v Edinburgh Academicals | Mannofield Park, Aberdeen | Results |
| 19 Jun 2011 | Third Round | Stenhousemuir v Watsonians | The Tryst, Stenhousemuir | Results |
| 03 Jul 2011 | Quarter Final | Watsonians v Ayr | Myreside, Edinburgh | Results |
| 03 Jul 2011 | Quarter Final | Aberdeenshire v Arbroath United | Mannofield Park, Aberdeen | Results |
| 03 Jul 2011 | Quarter Final | Uddingston v Clydesdale | Bothwell Castle, Uddingston | Results |
| 03 Jul 2011 | Quarter Final | Ferguslie v Dunfermline | Meikleriggs, Paisley | Results |
| 24 Jul 2011 | Semi Final | Watsonians v Uddingston | Myreside, Edinburgh | Results |
| 24 Jul 2011 | Semi Final | Dunfermline v Arbroath United | McKane Park, Dunfermline | Results |
| 20 Aug 2011 | Final | Uddingston v Dunfermline | Lochlands Park, Arbroath | Results |
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