| 27 May 1990 | Preliminary Round Section 1 | Stewart's Melville Former Pupils v West of Scotland | Inverleith, Edinburgh | Results |
| 27 May 1990 | Preliminary Round Section 1 | Cupar v Hawick and Wilton | Duffus Park, Cupar | Results |
| 27 May 1990 | Preliminary Round Section 2 | Edinburgh Academicals v Greenock | Edinburgh Academicals Ground, Raeburn Place, Edinburgh | Results |
| 27 May 1990 | Preliminary Round Section 2 | Forfarshire v Elgin | Forthill, Dundee | Results |
| 27 May 1990 | Preliminary Round Section 3 | Kelburne v Arbroath County | Whitehaugh Oval, Paisley | Results |
| 27 May 1990 | Preliminary Round Section 3 | Kirkcaldy v Northern Counties | Bennochy Park, Kirkcaldy | Results |
| 27 May 1990 | Preliminary Round Section 4 | Kelso v Clydesdale | Sheddon Park, Kelso | Results |
| 27 May 1990 | Preliminary Round Section 4 | Uddingston v Motherwell | Bothwell Castle, Uddingston | Results |
| 27 May 1990 | Preliminary Round Section 5 | Clackmannan County v Aberdeenshire | The Arns, Alloa | Results |
| 27 May 1990 | Preliminary Round Section 5 | Stenhousemuir v Meigle | The Tryst, Stenhousemuir | Results |
| 27 May 1990 | Preliminary Round Section 6 | Irvine v Drumpellier | Marress, Irvine | Results |
| 27 May 1990 | Preliminary Round Section 6 | Stirling County v East Kilbride | Williamfield, Stirling | Results |
| 27 May 1990 | Preliminary Round Section 7 | Perthshire v Heriot's Former Pupils | North Inch, Perth | Results |
| 27 May 1990 | Preliminary Round Section 7 | Strathmore County v Penicuik | Lochside Park, Forfar | Results |
| 27 May 1990 | Preliminary Round Section 8 | Dundee High School Former Pupils v Grange | Forthill, Dundee | Results |
| 27 May 1990 | Preliminary Round Section 8 | Ferguslie v Gordonians | Meikleriggs, Paisley | Results |
| 10 Jun 1990 | Preliminary Round Section 1 | West of Scotland v Cupar | Hamilton Crescent, Glasgow | Results |
| 10 Jun 1990 | Preliminary Round Section 1 | Hawick and Wilton v Stewart's Melville Former Pupils | Buccleuch Park, Hawick | Results |
| 10 Jun 1990 | Preliminary Round Section 2 | Greenock v Forfarshire | Glenpark, Greenock | Results |
| 10 Jun 1990 | Preliminary Round Section 2 | Elgin v Edinburgh Academicals | Cooper Park, Elgin | Results |
| 10 Jun 1990 | Preliminary Round Section 3 | Arbroath County v Kirkcaldy | Lochlands Park, Arbroath | Results |
| 10 Jun 1990 | Preliminary Round Section 3 | Northern Counties v Kelburne | Northern Meeting Park, Inverness | Results |
| 10 Jun 1990 | Preliminary Round Section 4 | Clydesdale v Uddingston | Titwood, Glasgow | Results |
| 10 Jun 1990 | Preliminary Round Section 4 | Motherwell v Kelso | Home Park, Motherwell | Results |
| 10 Jun 1990 | Preliminary Round Section 5 | Aberdeenshire v Stenhousemuir | Mannofield Park, Aberdeen | Results |
| 10 Jun 1990 | Preliminary Round Section 5 | Meigle v Clackmannan County | Victory Park, Meigle | Results |
| 10 Jun 1990 | Preliminary Round Section 6 | Drumpellier v Stirling County | Langloan, Coatbridge | Results |
| 10 Jun 1990 | Preliminary Round Section 6 | East Kilbride v Irvine | Torrance House, East Kilbride | Results |
| 10 Jun 1990 | Preliminary Round Section 7 | Heriot's Former Pupils v Strathmore County | Goldenacre, Edinburgh | Results |
| 10 Jun 1990 | Preliminary Round Section 7 | Penicuik v Perthshire | Kirkhill, Penicuik | Results |
| 10 Jun 1990 | Preliminary Round Section 8 | Grange v Ferguslie | Raeburn Place, Edinburgh | Results |
| 10 Jun 1990 | Preliminary Round Section 8 | Gordonians v Dundee High School Former Pupils | Slopefield, Aberdeen | Results |
| 24 Jun 1990 | Preliminary Round Section 1 | West of Scotland v Hawick and Wilton | Hamilton Crescent, Glasgow | Results |
| 24 Jun 1990 | Preliminary Round Section 1 | Cupar v Stewart's Melville Former Pupils | Duffus Park, Cupar | Results |
| 24 Jun 1990 | Preliminary Round Section 2 | Greenock v Elgin | Glenpark, Greenock | Results |
| 24 Jun 1990 | Preliminary Round Section 2 | Forfarshire v Edinburgh Academicals | Forthill, Dundee | Results |
| 24 Jun 1990 | Preliminary Round Section 3 | Arbroath County v Northern Counties | Lochlands Park, Arbroath | Results |
| 24 Jun 1990 | Preliminary Round Section 3 | Kirkcaldy v Kelburne | Bennochy Park, Kirkcaldy | Results |
| 24 Jun 1990 | Preliminary Round Section 4 | Clydesdale v Motherwell | Titwood, Glasgow | Results |
| 24 Jun 1990 | Preliminary Round Section 4 | Uddingston v Kelso | Bothwell Castle, Uddingston | Results |
| 24 Jun 1990 | Preliminary Round Section 5 | Aberdeenshire v Meigle | Mannofield Park, Aberdeen | Results |
| 24 Jun 1990 | Preliminary Round Section 5 | Stenhousemuir v Clackmannan County | The Tryst, Stenhousemuir | Results |
| 24 Jun 1990 | Preliminary Round Section 6 | Drumpellier v East Kilbride | Langloan, Coatbridge | Results |
| 24 Jun 1990 | Preliminary Round Section 6 | Stirling County v Irvine | Williamfield, Stirling | Results |
| 24 Jun 1990 | Preliminary Round Section 7 | Heriot's Former Pupils v Penicuik | Goldenacre, Edinburgh | Results |
| 24 Jun 1990 | Preliminary Round Section 7 | Strathmore County v Perthshire | Lochside Park, Forfar | Results |
| 24 Jun 1990 | Preliminary Round Section 8 | Grange v Gordonians | Raeburn Place, Edinburgh | Results |
| 24 Jun 1990 | Preliminary Round Section 8 | Ferguslie v Dundee High School Former Pupils | Meikleriggs, Paisley | Results |
| 08 Jul 1990 | Quarter-Final | not known v not known | not known | Results |
| 08 Jul 1990 | Quarter-Final | not known v not known | not known | Results |
| 08 Jul 1990 | Quarter-Final | not known v not known | not known | Results |
| 08 Jul 1990 | Quarter-Final | not known v not known | not known | Results |
| 05 Aug 1990 | Semi-Final | not known v not known | not known | Results |
| 05 Aug 1990 | Semi-Final | not known v not known | not known | Results |
| 26 Aug 1990 | Final | Grange v Strathmore | Hamilton Crescent, Glasgow | Results |
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