| 23 May 1999 | First Round | Fauldhouse Victoria v Old Contemptibles | Eastfield Park, Fauldhouse | Results |
| 23 May 1999 | First Round | Kirk Brae v Banchory | Kirk Brae Playing Fields, Edinburgh | Results |
| 23 May 1999 | First Round | Allan Glen's Former Pupils v Renfrew | The Bearyards, Bishopbriggs | Results |
| 23 May 1999 | First Round | Monklands v Doune | Langloan, Coatbridge | Results |
| 23 May 1999 | First Round | Manderston v Highland | Manderston, Duns | Results |
| 23 May 1999 | First Round | Castle Douglas v Kingsway | Castle Douglas Cricket Club Ground, Castle Douglas | Results |
| 23 May 1999 | First Round | Coupar Angus v Cramond | Larghan Park, Coupar | Results |
| 23 May 1999 | First Round | Jerviswood v Cumbernauld | Allanton Playing Fields, Ralston | Results |
| 23 May 1999 | First Round | Glendelvine v Edinburgh University Staff | Glendelvine Cricket Club Ground, Spittalfield | Results |
| 23 May 1999 | First Round | Keith v Dunnikier | Fife Park, Keith | Results |
| 23 May 1999 | First Round | Kinloch v Victoria | Lochee Park, Dundee | Results |
| 23 May 1999 | First Round | Largo v Ship Inn | East Drive, Upper Largo | Results |
| 23 May 1999 | First Round | Inverclyde v Royal Air Force Leuchars | Gourock Park, Gourock | Results |
| 23 May 1999 | First Round | Almond Valley v St Andrews University Staff | Druids Park, Murthly | Results |
| 23 May 1999 | First Round | Edinburgh Beige v Ardrossan | not known | Results |
| 23 May 1999 | First Round | Rouken Glen Young Men v Boroughmuir | Rouken Glen Park, Glasgow | Results |
| 23 May 1999 | First Round | Dunlop v Innellan | Netherhouses, Dunlop | Results |
| 23 May 1999 | First Round | Vale of Leven v Trinity Academicals | Millburn Park, Alexandria | Results |
| 23 May 1999 | First Round | Montrose v Dundee Asian | Union Park, Montrose | Results |
| 30 May 1999 | Second Round | Doune v Townhill | Moray Park, Doune | Results |
| 30 May 1999 | Second Round | Cumbernauld v Stonehaven Thistle | Cumbernauld Cricket Club Ground, Cumbernauld | Results |
| 30 May 1999 | Second Round | Cults v Luncarty | Allan Park, Cults | Results |
| 30 May 1999 | Second Round | Ship Inn v Cramond | Elie Beach, Elie | Results |
| 30 May 1999 | Second Round | Rouken Glen Young Men v Glendelvine | Rouken Glen Park, Glasgow | Results |
| 30 May 1999 | Second Round | Inverclyde v Kinloch | Gourock Park, Gourock | Results |
| 30 May 1999 | Second Round | Keith v Drummond | Fife Park, Keith | Results |
| 30 May 1999 | Second Round | Strathearn v Vale of Leven | Doo'cot Park No 1, Perth | Results |
| 30 May 1999 | Second Round | Renfrew v Ardrossan | King George V Playing Fields, Renfrew | Results |
| 30 May 1999 | Second Round | Ellon Gordon v Glasgow University Staff | Gordon Park, Ellon | Results |
| 30 May 1999 | Second Round | Castle Douglas v Rossie Priory | Castle Douglas Cricket Club Ground, Castle Douglas | Results |
| 30 May 1999 | Second Round | Queen's Park (Scotland) v Dunlop | Queen's Park, Glasgow | Results |
| 30 May 1999 | Second Round | Fauldhouse Victoria v Perth Mayfield | Eastfield Park, Fauldhouse | Results |
| 30 May 1999 | Second Round | Banchory v Buckie | Burnett Park, Banchory | Results |
| 30 May 1999 | Second Round | Manderston v St Andrews University Staff | Manderston, Duns | Results |
| 30 May 1999 | Second Round | Montrose v Westquarter and Redding | Union Park, Montrose | Results |
| 20 Jun 1999 | Third Round | Ellon Gordon v Perth Mayfield | Gordon Park, Ellon | Results |
| 20 Jun 1999 | Third Round | Cults v Townhill | Allan Park, Cults | Results |
| 20 Jun 1999 | Third Round | Renfrew v Vale of Leven | King George V Playing Fields, Renfrew | Results |
| 20 Jun 1999 | Third Round | Kinloch v Keith | Lochee Park, Dundee | Results |
| 20 Jun 1999 | Third Round | Cramond v Queen's Park (Scotland) | Cramond Campus, Edinburgh | Results |
| 20 Jun 1999 | Third Round | Montrose v Stonehaven Thistle | Union Park, Montrose | Results |
| 20 Jun 1999 | Third Round | Rossie Priory v Buckie | Rossie Priory, Inchture | Results |
| 20 Jun 1999 | Third Round | Glendelvine v Manderston | Glendelvine Cricket Club Ground, Spittalfield | Results |
| 04 Jul 1999 | Quarter-Final | Ellon Gordon v Keith | Gordon Park, Ellon | Results |
| 04 Jul 1999 | Quarter-Final | Rossie Priory v Stonehaven Thistle | Rossie Priory, Inchture | Results |
| 04 Jul 1999 | Quarter-Final | Cults v Glendelvine | Allan Park, Cults | Results |
| 04 Jul 1999 | Quarter-Final | Renfrew v Cramond | King George V Playing Fields, Renfrew | Results |
| 18 Jul 1999 | Semi-Final | Cults v Keith | Allan Park, Cults | Results |
| 18 Jul 1999 | Semi-Final | Renfrew v Stonehaven Thistle | King George V Playing Fields, Renfrew | Results |
| 08 Aug 1999 | Final | Cults v Stonehaven Thistle | Lochside Park, Forfar | Results |
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