| 01 Jun 2008 | First Round | Arbroath United v Stirling County | Lochlands Park, Arbroath | Results |
| 01 Jun 2008 | First Round | Ayr v Forfarshire | Cambusdoon New Ground, Alloway | Results |
| 01 Jun 2008 | First Round | Drumpellier v Ferguslie | Langloan, Coatbridge | Results |
| 01 Jun 2008 | First Round | Edinburgh v Aberdeenshire | Academy Park, Edinburgh | Results |
| 01 Jun 2008 | First Round | Greenock v Weirs | Glenpark, Greenock | Results |
| 01 Jun 2008 | First Round | Poloc v West of Scotland | Shawholm, Glasgow | Results |
| 01 Jun 2008 | First Round | Prestwick v Stoneywood-Dyce | Henry Thow Oval, Prestwick | Results |
| 01 Jun 2008 | First Round | Renfrew v Stenhousemuir | King George V Playing Fields, Renfrew | Results |
| 01 Jun 2008 | First Round | Royal High Corstorphine v Dunfermline | East Barnton Avenue, Edinburgh | Results |
| 08 Jun 2008 | First Round (replay) | Arbroath United v Stirling County | Lochlands Park, Arbroath | Results |
| 08 Jun 2008 | First Round (replay) | Ayr v Forfarshire | Cambusdoon New Ground, Alloway | Results |
| 08 Jun 2008 | First Round | Carlton v Clydesdale | Grange Loan, Edinburgh | Results |
| 08 Jun 2008 | First Round (replay) | Drumpellier v Ferguslie | Langloan, Coatbridge | Results |
| 08 Jun 2008 | First Round (replay) | Edinburgh v Aberdeenshire | Academy Park, Edinburgh | Results |
| 08 Jun 2008 | First Round | Grange v Freuchie | Raeburn Place, Edinburgh | Results |
| 08 Jun 2008 | First Round (replay) | Greenock v Weirs | Glenpark, Greenock | Results |
| 08 Jun 2008 | First Round | Heriot's v Dumfries | Goldenacre, Edinburgh | Results |
| 08 Jun 2008 | First Round | Penicuik v Stewart's Melville Royal High | Kirkhill, Penicuik | Results |
| 08 Jun 2008 | First Round (replay) | Poloc v West of Scotland | Shawholm, Glasgow | Results |
| 08 Jun 2008 | First Round (replay) | Royal High Corstorphine v Dunfermline | East Barnton Avenue, Edinburgh | Results |
| 08 Jun 2008 | First Round | West Lothian v Falkland | Boghall, Linlithgow | Results |
| 22 Jun 2008 | Second Round | Grange v Penicuik | Raeburn Place, Edinburgh | Results |
| 29 Jun 2008 | Second Round | Arbroath United v Clydesdale | Lochlands Park, Arbroath | Results |
| 29 Jun 2008 | Second Round | Dunfermline v Greenock | McKane Park, Dunfermline | Results |
| 29 Jun 2008 | Second Round | Forfarshire v Aberdeenshire | Forthill, Dundee | Results |
| 29 Jun 2008 | Second Round | Heriot's v Watsonians | Goldenacre, Edinburgh | Results |
| 29 Jun 2008 | Second Round | Prestwick v West of Scotland | Henry Thow Oval, Prestwick | Results |
| 29 Jun 2008 | Second Round | Stenhousemuir v Ferguslie | The Tryst, Stenhousemuir | Results |
| 29 Jun 2008 | Second Round | West Lothian v Uddingston | Boghall, Linlithgow | Results |
| 06 Jul 2008 | Quarter-Final | Forfarshire v Penicuik | Forthill, Dundee | Results |
| 06 Jul 2008 | Quarter-Final | Clydesdale v Greenock | Titwood, Glasgow | Results |
| 06 Jul 2008 | Quarter-Final | Prestwick v Ferguslie | Henry Thow Oval, Prestwick | Results |
| 20 Jul 2008 | Quarter-Final | Uddingston v Heriot's | Bothwell Castle, Uddingston | Results |
| 17 Aug 2008 | Semi-Final | Penicuik v Greenock | Kirkhill, Penicuik | Results |
| 17 Aug 2008 | Semi-Final | Uddingston v Ferguslie | Bothwell Castle, Uddingston | Results |
| 24 Aug 2008 | Final | Ferguslie v Penicuik | Bothwell Castle, Uddingston | Results |
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