| 21 May 2000 | First Round | Innellan v Glenrothes | Castle Toward, Toward | Results |
| 21 May 2000 | First Round | Boroughmuir v Almond Valley | Meggetland, Edinburgh | Results |
| 21 May 2000 | First Round | Perth Mayfield v Cramond | North Inch, Perth | Results |
| 21 May 2000 | First Round | Strathearn v Rouken Glen Young Men | Doo'cot Park No 1, Perth | Results |
| 21 May 2000 | First Round | Glasgow University Staff v Artisans | Garscube Estate, Glasgow | Results |
| 21 May 2000 | First Round | Coupar Angus v Drummond | Larghan Park, Coupar | Results |
| 21 May 2000 | First Round | Trinity Academicals v St Andrews University Staff | Bangholm Recreation Ground, Edinburgh | Results |
| 21 May 2000 | First Round | Kingsway v Montrose | University of Dundee Ground, Dundee | Results |
| 21 May 2000 | First Round | Marchmont v Dunlop | Cavalry Park, Edinburgh | Results |
| 21 May 2000 | First Round | Dunfermline Carnegie v Allan Glen's Former Pupils | Pitreavie Playing Fields, Dunfermline | Results |
| 21 May 2000 | First Round | Highland v Townhill | Fraser Park, Inverness | Results |
| 21 May 2000 | First Round | Inverclyde v Edinburgh University Staff | Gourock Park, Gourock | Results |
| 21 May 2000 | First Round | Old Grammarians v Ardrossan | Birkmyre Park, Kilmacolm | Results |
| 21 May 2000 | First Round | Ellon Gordon v Glendelvine | Gordon Park, Ellon | Results |
| 21 May 2000 | First Round | Kinloch v Luncarty | University Park, St Andrews | Results |
| 21 May 2000 | First Round | Manderston v Rossie Priory | Manderston, Duns | Results |
| 04 Jun 2000 | Second Round | Keith v Luncarty | Fife Park, Keith | Results |
| 04 Jun 2000 | Second Round | Dunfermline Carnegie v Breadalbane | Pitreavie Playing Fields, Dunfermline | Results |
| 04 Jun 2000 | Second Round | Almond Valley v Stonehaven Thistle | Druids Park, Murthly | Results |
| 04 Jun 2000 | Second Round | Buckie v Old Grammarians | Linzee Gordon Park, Buckie | Results |
| 04 Jun 2000 | Second Round | St Andrews University Staff v Renfrew | University Park, St Andrews | Results |
| 04 Jun 2000 | Second Round | Coupar Angus v Highland | Larghan Park, Coupar | Results |
| 04 Jun 2000 | Second Round | Largo v Cumbernauld | East Drive, Upper Largo | Results |
| 04 Jun 2000 | Second Round | Monklands v Marchmont | Langloan, Coatbridge | Results |
| 04 Jun 2000 | Second Round | Glenrothes v Doune | Riverside Park, Glenrothes | Results |
| 04 Jun 2000 | Second Round | Cults v Strathearn | Allan Park, Cults | Results |
| 04 Jun 2000 | Second Round | Jerviswood v Kingsway | Allanton Playing Fields, Ralston | Results |
| 04 Jun 2000 | Second Round | Inverclyde v Banchory | Gourock Park, Gourock | Results |
| 04 Jun 2000 | Second Round | Bon Accord v Rossie Priory | Duthie Park, Aberdeen | Results |
| 04 Jun 2000 | Second Round | Edinburgh Beige v Glasgow University Staff | not known | Results |
| 04 Jun 2000 | Second Round | Westquarter and Redding v Glendelvine | Bailliefields, Brightons | Results |
| 04 Jun 2000 | Second Round | Fauldhouse Victoria v Perth Mayfield | Eastfield Park, Fauldhouse | Results |
| 18 Jun 2000 | Third Round | Glendelvine v Fauldhouse Victoria | Glendelvine Cricket Club Ground, Spittalfield | Results |
| 18 Jun 2000 | Third Round | Renfrew v Edinburgh Beige | King George V Playing Fields, Renfrew | Results |
| 18 Jun 2000 | Third Round | Keith v Stonehaven Thistle | Fife Park, Keith | Results |
| 18 Jun 2000 | Third Round | Cults v Banchory | Allan Park, Cults | Results |
| 18 Jun 2000 | Third Round | Buckie v Monklands | Linzee Gordon Park, Buckie | Results |
| 18 Jun 2000 | Third Round | Dunfermline Carnegie v Kingsway | Pitreavie Playing Fields, Dunfermline | Results |
| 18 Jun 2000 | Third Round | Glenrothes v Highland | Riverside Park, Glenrothes | Results |
| 18 Jun 2000 | Third Round | Rossie Priory v Largo | Rossie Priory, Inchture | Results |
| 02 Jul 2000 | Quarter-Final | Keith v Rossie Priory | Fife Park, Keith | Results |
| 02 Jul 2000 | Quarter-Final | Glenrothes v Renfrew | Riverside Park, Glenrothes | Results |
| 02 Jul 2000 | Quarter-Final | Fauldhouse Victoria v Cults | Eastfield Park, Fauldhouse | Results |
| 02 Jul 2000 | Quarter-Final | Monklands v Dunfermline Carnegie | Langloan, Coatbridge | Results |
| 16 Jul 2000 | Semi-Final | Monklands v Rossie Priory | Langloan, Coatbridge | Results |
| 16 Jul 2000 | Semi-Final | Renfrew v Fauldhouse Victoria | King George V Playing Fields, Renfrew | Results |
| 30 Jul 2000 | Final | Renfrew v Rossie Priory | Lochside Park, Forfar | Results |
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