09 May 1999	Preliminary Round		Arbroath County v City of Edinburgh Pakistan Association	Lochlands Park, Arbroath	misc240736a
	09 May 1999	Preliminary Round	#	Gala v Uddingston	Meigle Park, Galashiels	misc240735
	30 May 1999	First Round	#	Arbroath County v Stenhousemuir	not known	misc240745
	30 May 1999	First Round	#	Brechin v Stewart's Melville Royal High	not known	misc240748
	30 May 1999	First Round		Corstorphine v Helensburgh	Union Park, Edinburgh	misc240739a
	30 May 1999	First Round	#	Dundee High School Former Pupils v Perth County	Forthill, Dundee	misc240742
	30 May 1999	First Round	#	Dunfermline v Dumfries	McKane Park, Dunfermline	misc240741
	30 May 1999	First Round		Falkland v Edinburgh Academicals	Scroggie Park, Falkland	misc240743a
	30 May 1999	First Round	#	Glasgow High Kelvinside v Holy Cross Academicals	not known	misc240751
	30 May 1999	First Round		Gordonians v Clydesdale	Slopefield, Aberdeen	misc240738a
	30 May 1999	First Round	#	Huntly v Penicuik	not known	misc240750
	30 May 1999	First Round	#	Inverurie v Livingston	Kellands Park, Inverurie	misc240752
	30 May 1999	First Round		Irvine v Kilmarnock	Marress, Irvine	misc
	30 May 1999	First Round	#	Kelburne v Selkirk	Whitehaugh Oval, Paisley	misc240749
	30 May 1999	First Round	#	Kelso v Forfarshire	Sheddon Park, Kelso	misc240747
	30 May 1999	First Round	#	Poloc v Uddingston	Shawholm, Glasgow	misc240746
	30 May 1999	First Round	#	Stirling County v Clackmannan County	not known	misc240737
	30 May 1999	First Round	#	Weirs v Cupar	Albert Park, Glasgow	misc240740
	20 Jun 1999	Second Round	#	Brechin v Kelso	not known	misc240758
	20 Jun 1999	Second Round	#	Clydesdale v Dunfermline	not known	misc240757
	20 Jun 1999	Second Round	#	Cupar v Glasgow High Kelvinside	not known	misc240756
	20 Jun 1999	Second Round		Falkland v Helensburgh	not known	misc240755a
	20 Jun 1999	Second Round	#	Huntly v Perth County	not known	misc240759
	20 Jun 1999	Second Round		Inverurie v Poloc	no ground arranged	misc240753a
	20 Jun 1999	Second Round	#	Irvine v Kelburne	not known	misc240760
	20 Jun 1999	Second Round	#	Stenhousemuir v Stirling County	not known	misc240754
	04 Jul 1999	Quarter-Final	#	Cupar v Huntly	not known	misc240764
	04 Jul 1999	Quarter-Final	#	Dunfermline v Poloc	not known	misc240761
	04 Jul 1999	Quarter-Final	#	Falkland v Kelburne	not known	misc240763
	04 Jul 1999	Quarter-Final		Kelso v Stirling County	not known	misc
	18 Jul 1999	Semi-Final	#	Huntly v Poloc	not known	misc240765
	18 Jul 1999	Semi-Final	#	Kelburne v Stirling County	not known	misc240766
	01 Aug 1999	Final		Poloc v Stirling County	Titwood, Glasgow	misc240767

The scorecards marked with a # are potted scores only.