| 07 May 2000 | Section One | Ayr v Freuchie | Cambusdoon New Ground, Alloway | Results |
| 07 May 2000 | Section One | Stirling County v Grange | Williamfield, Stirling | Results |
| 07 May 2000 | Section One | Clydesdale v Drumpellier | Titwood, Glasgow | Results |
| 21 May 2000 | Section One | Drumpellier v Ayr | Langloan, Coatbridge | Results |
| 21 May 2000 | Section One | Freuchie v Grange | The Park, Freuchie | Results |
| 21 May 2000 | Section One | Clydesdale v Stirling County | Titwood, Glasgow | Results |
| 04 Jun 2000 | Section One | Stirling County v Ayr | Williamfield, Stirling | Results |
| 04 Jun 2000 | Section One | Clydesdale v Grange | Titwood, Glasgow | Results |
| 04 Jun 2000 | Section One | Freuchie v Drumpellier | The Park, Freuchie | Results |
| 18 Jun 2000 | Section One | Ayr v Clydesdale | Cambusdoon New Ground, Alloway | Results |
| 18 Jun 2000 | Section One | Grange v Drumpellier | Raeburn Place, Edinburgh | Results |
| 18 Jun 2000 | Section One | Stirling County v Freuchie | Williamfield, Stirling | Results |
| 02 Jul 2000 | Section One | Grange v Ayr | Raeburn Place, Edinburgh | Results |
| 02 Jul 2000 | Section One | Clydesdale v Freuchie | Titwood, Glasgow | Results |
| 02 Jul 2000 | Section One | Drumpellier v Stirling County | Langloan, Coatbridge | Results |
| 07 May 2000 | Section Two | Aberdeenshire v Forfarshire | Mannofield Park, Aberdeen | Results |
| 07 May 2000 | Section Two | Stenhousemuir v Stoneywood-Dyce | The Tryst, Stenhousemuir | Results |
| 07 May 2000 | Section Two | Kelburne v West Lothian | Whitehaugh Oval, Paisley | Results |
| 21 May 2000 | Section Two | Forfarshire v West Lothian | Forthill, Dundee | Results |
| 21 May 2000 | Section Two | Stoneywood-Dyce v Kelburne | People's Park, Aberdeen | Results |
| 21 May 2000 | Section Two | Stenhousemuir v Aberdeenshire | The Tryst, Stenhousemuir | Results |
| 04 Jun 2000 | Section Two | Aberdeenshire v Kelburne | Mannofield Park, Aberdeen | Results |
| 04 Jun 2000 | Section Two | Stoneywood-Dyce v West Lothian | People's Park, Aberdeen | Results |
| 04 Jun 2000 | Section Two | Stenhousemuir v Forfarshire | The Tryst, Stenhousemuir | Results |
| 18 Jun 2000 | Section Two | Aberdeenshire v Stoneywood-Dyce | Mannofield Park, Aberdeen | Results |
| 18 Jun 2000 | Section Two | Stenhousemuir v West Lothian | The Tryst, Stenhousemuir | Results |
| 18 Jun 2000 | Section Two | Forfarshire v Kelburne | Forthill, Dundee | Results |
| 02 Jul 2000 | Section Two | Aberdeenshire v West Lothian | Mannofield Park, Aberdeen | Results |
| 02 Jul 2000 | Section Two | Kelburne v Stenhousemuir | Whitehaugh Oval, Paisley | Results |
| 02 Jul 2000 | Section Two | Stoneywood-Dyce v Forfarshire | People's Park, Aberdeen | Results |
| 07 May 2000 | Section Three | West of Scotland v Hillhead High School Former Pupils | Hamilton Crescent, Glasgow | Results |
| 07 May 2000 | Section Three | Dunfermline v Greenock | McKane Park, Dunfermline | Results |
| 07 May 2000 | Section Three | Prestwick v Watsonians | Henry Thow Oval, Prestwick | Results |
| 21 May 2000 | Section Three | Greenock v Hillhead High School Former Pupils | Glenpark, Greenock | Results |
| 21 May 2000 | Section Three | Dunfermline v Prestwick | McKane Park, Dunfermline | Results |
| 21 May 2000 | Section Three | West of Scotland v Watsonians | Hamilton Crescent, Glasgow | Results |
| 04 Jun 2000 | Section Three | Dunfermline v West of Scotland | McKane Park, Dunfermline | Results |
| 04 Jun 2000 | Section Three | Prestwick v Greenock | Henry Thow Oval, Prestwick | Results |
| 04 Jun 2000 | Section Three | Watsonians v Hillhead High School Former Pupils | Myreside, Edinburgh | Results |
| 18 Jun 2000 | Section Three | West of Scotland v Prestwick | Hamilton Crescent, Glasgow | Results |
| 18 Jun 2000 | Section Three | Watsonians v Greenock | Myreside, Edinburgh | Results |
| 18 Jun 2000 | Section Three | Hillhead High School Former Pupils v Dunfermline | Hughenden, Glasgow | Results |
| 02 Jul 2000 | Section Three | West of Scotland v Greenock | Hamilton Crescent, Glasgow | Results |
| 02 Jul 2000 | Section Three | Prestwick v Hillhead High School Former Pupils | Henry Thow Oval, Prestwick | Results |
| 02 Jul 2000 | Section Three | Dunfermline v Watsonians | McKane Park, Dunfermline | Results |
| 07 May 2000 | Section Four | Arbroath United v Heriot's | Lochlands Park, Arbroath | Results |
| 07 May 2000 | Section Four | Carlton v Falkland | Grange Loan, Edinburgh | Results |
| 07 May 2000 | Section Four | Uddingston v Ferguslie | Bothwell Castle, Uddingston | Results |
| 21 May 2000 | Section Four | Arbroath United v Carlton | Lochlands Park, Arbroath | Results |
| 21 May 2000 | Section Four | Heriot's v Uddingston | Goldenacre, Edinburgh | Results |
| 21 May 2000 | Section Four | Ferguslie v Falkland | Meikleriggs, Paisley | Results |
| 04 Jun 2000 | Section Four | Falkland v Heriot's | Scroggie Park, Falkland | Results |
| 04 Jun 2000 | Section Four | Carlton v Ferguslie | Grange Loan, Edinburgh | Results |
| 04 Jun 2000 | Section Four | Uddingston v Arbroath United | Bothwell Castle, Uddingston | Results |
| 18 Jun 2000 | Section Four | Ferguslie v Heriot's | Meikleriggs, Paisley | Results |
| 18 Jun 2000 | Section Four | Uddingston v Carlton | Bothwell Castle, Uddingston | Results |
| 18 Jun 2000 | Section Four | Falkland v Arbroath United | Scroggie Park, Falkland | Results |
| 02 Jul 2000 | Section Four | Heriot's v Carlton | Goldenacre, Edinburgh | Results |
| 02 Jul 2000 | Section Four | Ferguslie v Arbroath United | Meikleriggs, Paisley | Results |
| 02 Jul 2000 | Section Four | Uddingston v Falkland | Bothwell Castle, Uddingston | Results |
| 09 Jul 2000 | Quarter-Final | Ayr v Greenock | Cambusdoon New Ground, Alloway | Results |
| 09 Jul 2000 | Quarter-Final | Forfarshire v West of Scotland | Forthill, Dundee | Results |
| 09 Jul 2000 | Quarter-Final | Heriot's v West Lothian | Goldenacre, Edinburgh | Results |
| 09 Jul 2000 | Quarter-Final | Ferguslie v Grange | Meikleriggs, Paisley | Results |
| 30 Jul 2000 | Semi-Final | Heriot's v Forfarshire | Goldenacre, Edinburgh | Results |
| 30 Jul 2000 | Semi-Final | Ayr v Grange | Cambusdoon New Ground, Alloway | Results |
| 27 Aug 2000 | Final | Heriot's v Grange | Boghall, Linlithgow | Results |
| 03 Sep 2000 | Final | Heriot's v Grange | Boghall, Linlithgow | Results |
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