| 21 Jun 2009 | First Round | Aberdeenshire v Grange | Mannofield Park, Aberdeen | Results |
| 21 Jun 2009 | First Round | Ayr v Kelburne | Cambusdoon New Ground, Alloway | Results |
| 21 Jun 2009 | First Round | Dunfermline v Freuchie | McKane Park, Dunfermline | Results |
| 21 Jun 2009 | First Round | Edinburgh v Stoneywood-Dyce | Academy Park, Edinburgh | Results |
| 21 Jun 2009 | First Round | Edinburgh Academicals v Stewart's Melville Royal High | New Field, Edinburgh | Results |
| 21 Jun 2009 | First Round | Falkland v Heriot's | Scroggie Park, Falkland | Results |
| 21 Jun 2009 | First Round | Ferguslie v Stenhousemuir | Meikleriggs, Paisley | Results |
| 21 Jun 2009 | First Round | Penicuik v Forfarshire | Kirkhill, Penicuik | Results |
| 21 Jun 2009 | First Round | Poloc v Clydesdale | Shawholm, Glasgow | Results |
| 21 Jun 2009 | First Round | Prestwick v Dumfries | Henry Thow Oval, Prestwick | Results |
| 21 Jun 2009 | First Round | Renfrew v Drumpellier | King George V Playing Fields, Renfrew | Results |
| 21 Jun 2009 | First Round | Royal High Corstorphine v Arbroath United | East Barnton Avenue, Edinburgh | Results |
| 21 Jun 2009 | First Round | Stirling County v Greenock | New Williamfield, Stirling | Results |
| 21 Jun 2009 | First Round | Uddingston v Weirs | Bothwell Castle, Uddingston | Results |
| 21 Jun 2009 | First Round | Watsonians v Carlton | Myreside, Edinburgh | Results |
| 21 Jun 2009 | First Round | West Lothian v West of Scotland | Boghall, Linlithgow | Results |
| 12 Jul 2009 | Second Round | Aberdeenshire v Heriot's | Mannofield Park, Aberdeen | Results |
| 12 Jul 2009 | Second Round | Carlton v Arbroath United | Grange Loan, Edinburgh | Results |
| 12 Jul 2009 | Second Round | Ferguslie v Clydesdale | Meikleriggs, Paisley | Results |
| 12 Jul 2009 | Second Round | Forfarshire v Stewart's Melville Royal High | Forthill, Dundee | Results |
| 12 Jul 2009 | Second Round | West of Scotland v Ayr | Hamilton Crescent, Glasgow | Results |
| 12 Jul 2009 | Second Round | Prestwick v Dunfermline | Henry Thow Oval, Prestwick | Results |
| 12 Jul 2009 | Second Round | Renfrew v Greenock | King George V Playing Fields, Renfrew | Results |
| 12 Jul 2009 | Second Round | Uddingston v Edinburgh | Bothwell Castle, Uddingston | Results |
| 26 Jul 2009 | Quarter-Final | Greenock v Carlton | Glenpark, Greenock | Results |
| 02 Aug 2009 | Quarter-Final | Aberdeenshire v Ayr | Mannofield Park, Aberdeen | Results |
| 02 Aug 2009 | Quarter-Final | Dunfermline v Uddingston | McKane Park, Dunfermline | Results |
| 02 Aug 2009 | Quarter-Final | Forfarshire v Clydesdale | Forthill, Dundee | Results |
| 09 Aug 2009 | Semi-Final | Aberdeenshire v Clydesdale | Mannofield Park, Aberdeen | Results |
| 09 Aug 2009 | Semi-Final | Dunfermline v Greenock | McKane Park, Dunfermline | Results |
| 16 Aug 2009 | Semi-Final (replay) | Dunfermline v Greenock | McKane Park, Dunfermline | Results |
| 30 Aug 2009 | Final | Aberdeenshire v Dunfermline | Cambusdoon New Ground, Alloway | Results |
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