| 08 May 2016 | Preliminary Round | West of Scotland v Irvine | Hamilton Crescent, Glasgow | Results |
| 15 May 2016 | First Round | Drumpellier v Marchmont | Langloan, Coatbridge | Results |
| 15 May 2016 | First Round | Ayr v Forfarshire | Cambusdoon New Ground, Alloway | Results |
| 15 May 2016 | First Round | Poloc v Heriot's | Shawholm, Glasgow | Results |
| 15 May 2016 | First Round | Ferguslie v Weirs | Meikleriggs, Paisley | Results |
| 15 May 2016 | First Round | Dumfries v Glenrothes | Nunholm, Dumfries | Results |
| 15 May 2016 | First Round | Grange v Watsonians | Raeburn Place, Edinburgh | Results |
| 15 May 2016 | First Round | Dunnikier v Clydesdale | Dunnikier Park, Dunnikier | Results |
| 15 May 2016 | First Round | Uddingston v Renfrew | Bothwell Castle, Uddingston | Results |
| 15 May 2016 | First Round | Stirling County v Penicuik | New Williamfield, Stirling | Results |
| 15 May 2016 | First Round | Greenock v Stenhousemuir | Glenpark, Greenock | Results |
| 15 May 2016 | First Round | Glasgow Academicals v Falkland | New Anniesland, Glasgow | Results |
| 15 May 2016 | First Round | Prestwick v Carlton | Henry Thow Oval, Prestwick | Results |
| 15 May 2016 | First Round | Aberdeenshire v Kelburne | Mannofield Park, Aberdeen | Results |
| 15 May 2016 | First Round | East Kilbride v Meigle | Torrance House, East Kilbride | Results |
| 15 May 2016 | First Round | Stewart's Melville Royal High v Arbroath United | Inverleith, Edinburgh | Results |
| 15 May 2016 | First Round | Stoneywood-Dyce v West of Scotland | People's Park, Aberdeen | Results |
| 05 Jun 2016 | Second Round | Drumpellier v Forfarshire | Langloan, Coatbridge | Results |
| 05 Jun 2016 | Second Round | Heriot's v Ferguslie | Goldenacre, Edinburgh | Results |
| 05 Jun 2016 | Second Round | Glenrothes v Grange | Riverside Park, Glenrothes | Results |
| 05 Jun 2016 | Second Round | Clydesdale v Uddingston | Titwood, Glasgow | Results |
| 05 Jun 2016 | Second Round | Stirling County v Greenock | New Williamfield, Stirling | Results |
| 05 Jun 2016 | Second Round | Falkland v Carlton | Scroggie Park, Falkland | Results |
| 05 Jun 2016 | Second Round | Aberdeenshire v East Kilbride | Mannofield Park, Aberdeen | Results |
| 05 Jun 2016 | Second Round | Arbroath United v West of Scotland | Lochlands Park, Arbroath | Results |
| 26 Jun 2016 | Quarter-Final | Grange v Clydesdale | Raeburn Place, Edinburgh | Results |
| 26 Jun 2016 | Quarter-Final | East Kilbride v Arbroath United | Torrance House, East Kilbride | Results |
| 03 Jul 2016 | Quarter-Final | Ferguslie v Drumpellier | Meikleriggs, Paisley | Results |
| 12 Jul 2016 | Quarter-Final | Greenock v Carlton | Glenpark, Greenock | Results |
| 17 Jul 2016 | Semi-Final | Ferguslie v Clydesdale | Meikleriggs, Paisley | Results |
| 17 Jul 2016 | Semi-Final | Carlton v Arbroath United | Grange Loan, Edinburgh | Results |
| 21 Aug 2016 | Final | Arbroath United v Clydesdale | Hamilton Crescent, Glasgow | Results |
| 03 Jul 2016 | Quarter-Final | Clydesdale v Grange | Titwood, Glasgow | Results |
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