| 28 May 1989 | Preliminary Round Section 1 | Arbroath United v West of Scotland | Lochlands Park, Arbroath | Results |
| 28 May 1989 | Preliminary Round Section 1 | Ayrshire v Woodhall | Henry Thow Oval, Prestwick | Results |
| 28 May 1989 | Preliminary Round Section 2 | Clackmannan County v Ayr | The Arns, Alloa | Results |
| 28 May 1989 | Preliminary Round Section 2 | Kirkcaldy v Huntly | Bennochy Park, Kirkcaldy | Results |
| 28 May 1989 | Preliminary Round Section 3 | Uddingston v Stenhousemuir | Bothwell Castle, Uddingston | Results |
| 28 May 1989 | Preliminary Round Section 3 | Heriot's Former Pupils v Hawick and Wilton | Goldenacre, Edinburgh | Results |
| 28 May 1989 | Preliminary Round Section 4 | Strathmore County v Greenock | Lochside Park, Forfar | Results |
| 28 May 1989 | Preliminary Round Section 4 | Forfarshire v Dundee High School Former Pupils | Forthill, Dundee | Results |
| 28 May 1989 | Preliminary Round Section 5 | Kelso v Carlton | Sheddon Park, Kelso | Results |
| 28 May 1989 | Preliminary Round Section 5 | Poloc v Northern Counties | Shawholm, Glasgow | Results |
| 28 May 1989 | Preliminary Round Section 6 | Royal High v Clydesdale | Jock's Lodge, Edinburgh | Results |
| 28 May 1989 | Preliminary Round Section 6 | Grange v Helensburgh | Raeburn Place, Edinburgh | Results |
| 28 May 1989 | Preliminary Round Section 7 | Irvine v Perth County | Marress, Irvine | Results |
| 28 May 1989 | Preliminary Round Section 7 | Stirling County v Brechin | Williamfield, Stirling | Results |
| 28 May 1989 | Preliminary Round Section 8 | Freuchie v Aberdeenshire | The Park, Freuchie | Results |
| 28 May 1989 | Preliminary Round Section 8 | Drumpellier v Berwick | Langloan, Coatbridge | Results |
| 11 Jun 1989 | Preliminary Round Section 1 | West of Scotland v Ayrshire | Hamilton Crescent, Glasgow | Results |
| 11 Jun 1989 | Preliminary Round Section 1 | Woodhall v Arbroath United | Maggies Haugh, Woodhall | Results |
| 11 Jun 1989 | Preliminary Round Section 2 | Ayr v Kirkcaldy | Cambusdoon, Alloway | Results |
| 11 Jun 1989 | Preliminary Round Section 2 | Huntly v Clackmannan County | Castle Park, Huntly | Results |
| 11 Jun 1989 | Preliminary Round Section 3 | Stenhousemuir v Heriot's Former Pupils | The Tryst, Stenhousemuir | Results |
| 11 Jun 1989 | Preliminary Round Section 3 | Hawick and Wilton v Uddingston | Buccleuch Park, Hawick | Results |
| 11 Jun 1989 | Preliminary Round Section 4 | Greenock v Forfarshire | Glenpark, Greenock | Results |
| 11 Jun 1989 | Preliminary Round Section 4 | Dundee High School Former Pupils v Strathmore County | Forthill, Dundee | Results |
| 11 Jun 1989 | Preliminary Round Section 5 | Carlton v Poloc | Grange Loan, Edinburgh | Results |
| 11 Jun 1989 | Preliminary Round Section 5 | Northern Counties v Kelso | Northern Meeting Park, Inverness | Results |
| 11 Jun 1989 | Preliminary Round Section 6 | Clydesdale v Grange | Titwood, Glasgow | Results |
| 11 Jun 1989 | Preliminary Round Section 6 | Helensburgh v Royal High | Ardencaple, Helensburgh | Results |
| 11 Jun 1989 | Preliminary Round Section 7 | Perth County v Stirling County | North Inch, Perth | Results |
| 11 Jun 1989 | Preliminary Round Section 7 | Brechin v Irvine | Guthrie Park, Brechin | Results |
| 11 Jun 1989 | Preliminary Round Section 8 | Aberdeenshire v Drumpellier | Mannofield Park, Aberdeen | Results |
| 11 Jun 1989 | Preliminary Round Section 8 | Berwick v Freuchie | Pier Field, Berwick-upon-Tweed | Results |
| 25 Jun 1989 | Preliminary Round Section 1 | West of Scotland v Woodhall | Hamilton Crescent, Glasgow | Results |
| 25 Jun 1989 | Preliminary Round Section 1 | Ayrshire v Arbroath United | Henry Thow Oval, Prestwick | Results |
| 25 Jun 1989 | Preliminary Round Section 2 | Ayr v Huntly | Cambusdoon, Alloway | Results |
| 25 Jun 1989 | Preliminary Round Section 2 | Kirkcaldy v Clackmannan County | Bennochy Park, Kirkcaldy | Results |
| 25 Jun 1989 | Preliminary Round Section 3 | Stenhousemuir v Hawick and Wilton | The Tryst, Stenhousemuir | Results |
| 25 Jun 1989 | Preliminary Round Section 3 | Heriot's Former Pupils v Uddingston | Goldenacre, Edinburgh | Results |
| 25 Jun 1989 | Preliminary Round Section 4 | Greenock v Dundee High School Former Pupils | Glenpark, Greenock | Results |
| 25 Jun 1989 | Preliminary Round Section 4 | Forfarshire v Strathmore County | Forthill, Dundee | Results |
| 25 Jun 1989 | Preliminary Round Section 5 | Carlton v Northern Counties | Grange Loan, Edinburgh | Results |
| 25 Jun 1989 | Preliminary Round Section 5 | Poloc v Kelso | Shawholm, Glasgow | Results |
| 25 Jun 1989 | Preliminary Round Section 6 | Clydesdale v Helensburgh | Titwood, Glasgow | Results |
| 25 Jun 1989 | Preliminary Round Section 6 | Grange v Royal High | Raeburn Place, Edinburgh | Results |
| 25 Jun 1989 | Preliminary Round Section 7 | Perth County v Brechin | North Inch, Perth | Results |
| 25 Jun 1989 | Preliminary Round Section 7 | Stirling County v Irvine | Williamfield, Stirling | Results |
| 25 Jun 1989 | Preliminary Round Section 8 | Aberdeenshire v Berwick | Mannofield Park, Aberdeen | Results |
| 25 Jun 1989 | Preliminary Round Section 8 | Drumpellier v Freuchie | Langloan, Coatbridge | Results |
| 16 Jul 1989 | Quarter-Final | not known v not known | not known | Results |
| 16 Jul 1989 | Quarter-Final | not known v not known | not known | Results |
| 16 Jul 1989 | Quarter-Final | not known v not known | not known | Results |
| 16 Jul 1989 | Quarter-Final | not known v not known | not known | Results |
| 06 Aug 1989 | Semi-Final | not known v not known | not known | Results |
| 06 Aug 1989 | Semi-Final | not known v not known | not known | Results |
| 27 Aug 1989 | Final | Clydesdale v West of Scotland | Hamilton Crescent, Glasgow | Results |
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