| 08 May 1988 | Preliminary Round Section 1 | Drumpellier v Kelso | Langloan, Coatbridge | Results |
| 08 May 1988 | Preliminary Round Section 1 | Irvine v Aberdeenshire | Marress, Irvine | Results |
| 08 May 1988 | Preliminary Round Section 2 | Gala v Greenock | Meigle Park, Galashiels | Results |
| 08 May 1988 | Preliminary Round Section 2 | Forfarshire v Motherwell | Forthill, Dundee | Results |
| 08 May 1988 | Preliminary Round Section 3 | Ayr v Huntly | Cambusdoon, Alloway | Results |
| 08 May 1988 | Preliminary Round Section 3 | Arbroath United v Ayrshire | Lochlands Park, Arbroath | Results |
| 08 May 1988 | Preliminary Round Section 4 | Northern Counties v Clydesdale | Northern Meeting Park, Inverness | Results |
| 08 May 1988 | Preliminary Round Section 4 | Perthshire v Aberdeen Grammar School Former Pupils | North Inch, Perth | Results |
| 22 May 1988 | Preliminary Round Section 1 | Drumpellier v Royal High | Langloan, Coatbridge | Results |
| 22 May 1988 | Preliminary Round Section 1 | Aberdeenshire v Kelso | Mannofield Park, Aberdeen | Results |
| 22 May 1988 | Preliminary Round Section 2 | Grange v Greenock | Raeburn Place, Edinburgh | Results |
| 22 May 1988 | Preliminary Round Section 2 | Gala v Forfarshire | Meigle Park, Galashiels | Results |
| 22 May 1988 | Preliminary Round Section 3 | Ayr v Stenhousemuir | Cambusdoon, Alloway | Results |
| 22 May 1988 | Preliminary Round Section 3 | Ayrshire v Huntly | Henry Thow Oval, Prestwick | Results |
| 22 May 1988 | Preliminary Round Section 4 | Carlton v Clydesdale | Grange Loan, Edinburgh | Results |
| 22 May 1988 | Preliminary Round Section 4 | Northern Counties v Perthshire | Northern Meeting Park, Inverness | Results |
| 26 Jun 1988 | Preliminary Round Section 1 | Royal High v Aberdeenshire | Jock's Lodge, Edinburgh | Results |
| 26 Jun 1988 | Preliminary Round Section 1 | Kelso v Irvine | Sheddon Park, Kelso | Results |
| 26 Jun 1988 | Preliminary Round Section 2 | Forfarshire v Grange | Forthill, Dundee | Results |
| 26 Jun 1988 | Preliminary Round Section 2 | Motherwell v Gala | Home Park, Motherwell | Results |
| 26 Jun 1988 | Preliminary Round Section 3 | Stenhousemuir v Ayrshire | The Tryst, Stenhousemuir | Results |
| 26 Jun 1988 | Preliminary Round Section 3 | Huntly v Arbroath United | Castle Park, Huntly | Results |
| 26 Jun 1988 | Preliminary Round Section 4 | Perthshire v Carlton | North Inch, Perth | Results |
| 26 Jun 1988 | Preliminary Round Section 4 | Aberdeen Grammar School Former Pupils v Northern Counties | Rubislaw Field, Aberdeen | Results |
| 03 Jul 1988 | Preliminary Round Section 1 | Irvine v Drumpellier | Marress, Irvine | Results |
| 03 Jul 1988 | Preliminary Round Section 1 | Kelso v Royal High | Sheddon Park, Kelso | Results |
| 03 Jul 1988 | Preliminary Round Section 2 | Greenock v Motherwell | Glenpark, Greenock | Results |
| 03 Jul 1988 | Preliminary Round Section 2 | Grange v Gala | Raeburn Place, Edinburgh | Results |
| 03 Jul 1988 | Preliminary Round Section 3 | Arbroath United v Ayr | Lochlands Park, Arbroath | Results |
| 03 Jul 1988 | Preliminary Round Section 3 | Huntly v Stenhousemuir | Castle Park, Huntly | Results |
| 03 Jul 1988 | Preliminary Round Section 4 | Clydesdale v Aberdeen Grammar School Former Pupils | Titwood, Glasgow | Results |
| 03 Jul 1988 | Preliminary Round Section 4 | Carlton v Northern Counties | Grange Loan, Edinburgh | Results |
| 10 Jul 1988 | Preliminary Round Section 1 | Aberdeenshire v Drumpellier | Mannofield Park, Aberdeen | Results |
| 10 Jul 1988 | Preliminary Round Section 1 | Royal High v Irvine | Jock's Lodge, Edinburgh | Results |
| 10 Jul 1988 | Preliminary Round Section 2 | Greenock v Forfarshire | Glenpark, Greenock | Results |
| 10 Jul 1988 | Preliminary Round Section 2 | Motherwell v Grange | Home Park, Motherwell | Results |
| 10 Jul 1988 | Preliminary Round Section 3 | Ayrshire v Ayr | Henry Thow Oval, Prestwick | Results |
| 10 Jul 1988 | Preliminary Round Section 3 | Stenhousemuir v Arbroath United | The Tryst, Stenhousemuir | Results |
| 10 Jul 1988 | Preliminary Round Section 4 | Clydesdale v Perthshire | Titwood, Glasgow | Results |
| 10 Jul 1988 | Preliminary Round Section 4 | Aberdeen Grammar School Former Pupils v Carlton | Rubislaw Field, Aberdeen | Results |
| 24 Jul 1988 | Quarter-Final | not known v not known | not known | Results |
| 24 Jul 1988 | Quarter-Final | not known v not known | not known | Results |
| 24 Jul 1988 | Quarter-Final | not known v not known | not known | Results |
| 24 Jul 1988 | Quarter-Final | not known v not known | not known | Results |
| 07 Aug 1988 | Semi-Final | not known v not known | not known | Results |
| 07 Aug 1988 | Semi-Final | not known v not known | not known | Results |
| 04 Sep 1988 | Final | Aberdeen Grammar School Former Pupils v Clydesdale | Lochside Park, Forfar | Results |
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