| 14 Jun 1987 | Preliminary Round Section 1 | Uddingston v Selkirk | Bothwell Castle, Uddingston | Results |
| 14 Jun 1987 | Preliminary Round Section 1 | North Kelvinside Old Aloysians v Strathmore County | St Aloysius College Ground, Glasgow | Results |
| 21 Jun 1987 | Preliminary Round Section 1 | Uddingston v Kirkcaldy | Bothwell Castle, Uddingston | Results |
| 21 Jun 1987 | Preliminary Round Section 1 | Strathmore County v Selkirk | Lochside Park, Forfar | Results |
| 28 Jun 1987 | Preliminary Round Section 1 | Kirkcaldy v Strathmore County | Bennochy Park, Kirkcaldy | Results |
| 28 Jun 1987 | Preliminary Round Section 1 | Selkirk v North Kelvinside Old Aloysians | Philiphaugh, Selkirk | Results |
| 05 Jul 1987 | Preliminary Round Section 1 | North Kelvinside Old Aloysians v Uddingston | St Aloysius College Ground, Glasgow | Results |
| 05 Jul 1987 | Preliminary Round Section 1 | Selkirk v Kirkcaldy | Philiphaugh, Selkirk | Results |
| 12 Jul 1987 | Preliminary Round Section 1 | Strathmore County v Uddingston | Lochside Park, Forfar | Results |
| 12 Jul 1987 | Preliminary Round Section 1 | Kirkcaldy v North Kelvinside Old Aloysians | Bennochy Park, Kirkcaldy | Results |
| 14 Jun 1987 | Preliminary Round Section 2 | Kelso v Ferguslie | Sheddon Park, Kelso | Results |
| 14 Jun 1987 | Preliminary Round Section 2 | Perth County v Irvine | North Inch, Perth | Results |
| 21 Jun 1987 | Preliminary Round Section 2 | Stenhousemuir v Ferguslie | The Tryst, Stenhousemuir | Results |
| 21 Jun 1987 | Preliminary Round Section 2 | Kelso v Perth County | Sheddon Park, Kelso | Results |
| 28 Jun 1987 | Preliminary Round Section 2 | Perth County v Stenhousemuir | North Inch, Perth | Results |
| 28 Jun 1987 | Preliminary Round Section 2 | Irvine v Kelso | Marress, Irvine | Results |
| 05 Jul 1987 | Preliminary Round Section 2 | Ferguslie v Irvine | Meikleriggs, Paisley | Results |
| 05 Jul 1987 | Preliminary Round Section 2 | Stenhousemuir v Kelso | The Tryst, Stenhousemuir | Results |
| 12 Jul 1987 | Preliminary Round Section 2 | Ferguslie v Perth County | Meikleriggs, Paisley | Results |
| 12 Jul 1987 | Preliminary Round Section 2 | Irvine v Stenhousemuir | Marress, Irvine | Results |
| 14 Jun 1987 | Preliminary Round Section 3 | Clydesdale v Huntly | Titwood, Glasgow | Results |
| 14 Jun 1987 | Preliminary Round Section 3 | Arbroath United v Aberdeenshire | Lochlands Park, Arbroath | Results |
| 21 Jun 1987 | Preliminary Round Section 3 | Clydesdale v Cupar | Titwood, Glasgow | Results |
| 21 Jun 1987 | Preliminary Round Section 3 | Aberdeenshire v Huntly | Mannofield Park, Aberdeen | Results |
| 28 Jun 1987 | Preliminary Round Section 3 | Cupar v Aberdeenshire | Duffus Park, Cupar | Results |
| 28 Jun 1987 | Preliminary Round Section 3 | Huntly v Arbroath United | Castle Park, Huntly | Results |
| 05 Jul 1987 | Preliminary Round Section 3 | Arbroath United v Clydesdale | Lochlands Park, Arbroath | Results |
| 05 Jul 1987 | Preliminary Round Section 3 | Huntly v Cupar | Castle Park, Huntly | Results |
| 12 Jul 1987 | Preliminary Round Section 3 | Aberdeenshire v Clydesdale | Mannofield Park, Aberdeen | Results |
| 12 Jul 1987 | Preliminary Round Section 3 | Cupar v Arbroath United | Duffus Park, Cupar | Results |
| 14 Jun 1987 | Preliminary Round Section 4 | Northern Counties v Greenock | Northern Meeting Park, Inverness | Results |
| 14 Jun 1987 | Preliminary Round Section 4 | Ayrshire v Brechin | Henry Thow Oval, Prestwick | Results |
| 21 Jun 1987 | Preliminary Round Section 4 | Carlton v Greenock | Grange Loan, Edinburgh | Results |
| 21 Jun 1987 | Preliminary Round Section 4 | Northern Counties v Ayrshire | Northern Meeting Park, Inverness | Results |
| 28 Jun 1987 | Preliminary Round Section 4 | Ayrshire v Carlton | Henry Thow Oval, Prestwick | Results |
| 28 Jun 1987 | Preliminary Round Section 4 | Brechin v Northern Counties | Guthrie Park, Brechin | Results |
| 05 Jul 1987 | Preliminary Round Section 4 | Greenock v Brechin | Glenpark, Greenock | Results |
| 05 Jul 1987 | Preliminary Round Section 4 | Carlton v Northern Counties | Grange Loan, Edinburgh | Results |
| 12 Jul 1987 | Preliminary Round Section 4 | Brechin v Carlton | Guthrie Park, Brechin | Results |
| 12 Jul 1987 | Preliminary Round Section 4 | Greenock v Ayrshire | Glenpark, Greenock | Results |
| 26 Jul 1987 | Quarter-Final | not known v not known | not known | Results |
| 26 Jul 1987 | Quarter-Final | not known v not known | not known | Results |
| 26 Jul 1987 | Quarter-Final | not known v not known | not known | Results |
| 26 Jul 1987 | Quarter-Final | not known v not known | not known | Results |
| 09 Aug 1987 | Semi-Final | not known v not known | not known | Results |
| 09 Aug 1987 | Semi-Final | not known v not known | not known | Results |
| 30 Aug 1987 | Final | Clydesdale v Perthshire | Hamilton Crescent, Glasgow | Results |
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