| 24 May 1998 | First Round | Old Contemptibles v Leith Franklin Academicals | Inverleith, Edinburgh | Results |
| 24 May 1998 | First Round | Dundee University Staff v Monklands | not known | Results |
| 24 May 1998 | First Round | Keith v Westquarter and Redding | Fife Park, Keith | Results |
| 24 May 1998 | First Round | Huntly v Vale of Leven | Castle Park, Huntly | Results |
| 24 May 1998 | First Round | Dunlop v Perth Mayfield | Netherhouses, Dunlop | Results |
| 24 May 1998 | First Round | Queen's Park (Scotland) v Elgin | Queen's Park, Glasgow | Results |
| 24 May 1998 | First Round | Dunnikier v Coupar Angus | Dunnikier Park, Dunnikier | Results |
| 24 May 1998 | First Round | Innellan v Townhill | Castle Toward, Toward | Results |
| 24 May 1998 | First Round | Jerviswood v Kinloch | Allanton Playing Fields, Ralston | Results |
| 24 May 1998 | First Round | Rouken Glen Young Men v Rossie Priory | Rouken Glen Park, Glasgow | Results |
| 24 May 1998 | First Round | Ship Inn v Highland | Elie Beach, Elie | Results |
| 24 May 1998 | First Round | Cumbernauld v Strathearn | Cumbernauld Cricket Club Ground, Cumbernauld | Results |
| 24 May 1998 | First Round | Cramond v Ardrossan | Cramond Campus, Edinburgh | Results |
| 24 May 1998 | First Round | Artisans v Kingsway | Harlaw Playing Field, Aberdeen | Results |
| 24 May 1998 | First Round | Drummond v Stonehaven Thistle | Inverleith, Edinburgh | Results |
| 24 May 1998 | First Round | Renfrew v Glendelvine | King George V Playing Fields, Renfrew | Results |
| 24 May 1998 | First Round | Largo v Peebles County | East Drive, Upper Largo | Results |
| 24 May 1998 | First Round | Glasgow University Staff v Royal Air Force Lossiemouth | Garscube Estate, Glasgow | Results |
| 24 May 1998 | First Round | Manderston v Doune | Manderston, Duns | Results |
| 24 May 1998 | First Round | Ellon Gordon v Crieff | Gordon Park, Ellon | Results |
| 24 May 1998 | First Round | St Andrews University Staff v Montrose | University Park, St Andrews | Results |
| 24 May 1998 | First Round | Forres St Lawrence v Breadalbane | Grant Park, Forres | Results |
| 07 Jun 1998 | Second Round | Banchory v Cramond | Burnett Park, Banchory | Results |
| 07 Jun 1998 | Second Round | Forres St Lawrence v Highland | Grant Park, Forres | Results |
| 07 Jun 1998 | Second Round | Luncarty v Perth Mayfield | Langlands Park, Luncarty | Results |
| 07 Jun 1998 | Second Round | Queen's Park (Scotland) v Strathearn | Queen's Park, Glasgow | Results |
| 07 Jun 1998 | Second Round | Buckie v Renfrew | Linzee Gordon Park, Buckie | Results |
| 07 Jun 1998 | Second Round | Victoria v Leith Franklin Academicals | Victoria Park, Glasgow | Results |
| 07 Jun 1998 | Second Round | Coupar Angus v Largo | Larghan Park, Coupar | Results |
| 07 Jun 1998 | Second Round | Keith v Dalgety Bay | Fife Park, Keith | Results |
| 07 Jun 1998 | Second Round | Manderston v Montrose | Manderston, Duns | Results |
| 07 Jun 1998 | Second Round | Cults v Edinburgh Beige | Allan Park, Cults | Results |
| 07 Jun 1998 | Second Round | Fauldhouse Victoria v Glasgow University Staff | Eastfield Park, Fauldhouse | Results |
| 07 Jun 1998 | Second Round | Jerviswood v Inverclyde | Allanton Playing Fields, Ralston | Results |
| 07 Jun 1998 | Second Round | Rossie Priory v Ellon Gordon | Rossie Priory, Inchture | Results |
| 07 Jun 1998 | Second Round | Monklands v Stonehaven Thistle | Langloan, Coatbridge | Results |
| 07 Jun 1998 | Second Round | Huntly v Townhill | Castle Park, Huntly | Results |
| 07 Jun 1998 | Second Round | Artisans v Trinity Academicals | Harlaw Playing Field, Aberdeen | Results |
| 21 Jun 1998 | Third Round | Rossie Priory v Artisans | Rossie Priory, Inchture | Results |
| 21 Jun 1998 | Third Round | Highland v Coupar Angus | Fraser Park, Inverness | Results |
| 21 Jun 1998 | Third Round | Buckie v Queen's Park (Scotland) | Linzee Gordon Park, Buckie | Results |
| 21 Jun 1998 | Third Round | Townhill v Manderston | Recreation Park, Townhill | Results |
| 21 Jun 1998 | Third Round | Monklands v Leith Franklin Academicals | Langloan, Coatbridge | Results |
| 21 Jun 1998 | Third Round | Keith v Jerviswood | Fife Park, Keith | Results |
| 21 Jun 1998 | Third Round | Luncarty v Cults | Langlands Park, Luncarty | Results |
| 21 Jun 1998 | Third Round | Banchory v Fauldhouse Victoria | Burnett Park, Banchory | Results |
| 05 Jul 1998 | Quarter-Final | Highland v Rossie Priory | Fraser Park, Inverness | Results |
| 05 Jul 1998 | Quarter-Final | Queen's Park (Scotland) v Manderston | Queen's Park, Glasgow | Results |
| 05 Jul 1998 | Quarter-Final | Leith Franklin v Keith | Leith Links, Edinburgh | Results |
| 05 Jul 1998 | Quarter-Final | Cults v Banchory | Allan Park, Cults | Results |
| 19 Jul 1998 | Semi-Final | Rossie Priory v Cults | Rossie Priory, Inchture | Results |
| 19 Jul 1998 | Semi-Final | Leith Franklin Academicals v Queen's Park (Scotland) | Leith Links, Edinburgh | Results |
| 09 Aug 1998 | Final | Cults v Queen's Park (Scotland) | Lochside Park, Forfar | Results |
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