23 May 1999	First Round	#	Allan Glen's Former Pupils v Renfrew	The Bearyards, Bishopbriggs	misc243579
	23 May 1999	First Round	#	Almond Valley v St Andrews University Staff	Druids Park, Murthly	misc243590
	23 May 1999	First Round	#	Castle Douglas v Kingsway	Castle Douglas Cricket Club Ground, Castle Douglas	misc243582
	23 May 1999	First Round	#	Coupar Angus v Cramond	Larghan Park, Coupar	misc243583
	23 May 1999	First Round		Dunlop v Innellan	Netherhouses, Dunlop	misc243593a
	23 May 1999	First Round	#	Edinburgh Beige v Ardrossan	not known	misc243591
	23 May 1999	First Round		Fauldhouse Victoria v Old Contemptibles	Eastfield Park, Fauldhouse	misc243577a
	23 May 1999	First Round	#	Glendelvine v Edinburgh University Staff	Glendelvine Cricket Club Ground, Spittalfield	misc243585
	23 May 1999	First Round	#	Inverclyde v Royal Air Force Leuchars	Gourock Park, Gourock	misc243589
	23 May 1999	First Round	#	Jerviswood v Cumbernauld	Allanton Playing Fields, Ralston	misc243584
	23 May 1999	First Round	#	Keith v Dunnikier	Fife Park, Keith	misc243586
	23 May 1999	First Round		Kinloch v Victoria	Lochee Park, Dundee	misc243587a
	23 May 1999	First Round	#	Kirk Brae v Banchory	Kirk Brae Playing Fields, Edinburgh	misc243578
	23 May 1999	First Round	#	Largo v Ship Inn	East Drive, Upper Largo	misc243588
	23 May 1999	First Round	#	Manderston v Highland	Manderston, Duns	misc243581
	23 May 1999	First Round	#	Monklands v Doune	Langloan, Coatbridge	misc243580
	23 May 1999	First Round		Montrose v Dundee Asian	Union Park, Montrose	misc243595a
	23 May 1999	First Round		Rouken Glen Young Men v Boroughmuir	Rouken Glen Park, Glasgow	misc243592a
	23 May 1999	First Round		Vale of Leven v Trinity Academicals	Millburn Park, Alexandria	misc
	30 May 1999	Second Round	#	Banchory v Buckie	Burnett Park, Banchory	misc243609
	30 May 1999	Second Round	#	Castle Douglas v Rossie Priory	Castle Douglas Cricket Club Ground, Castle Douglas	misc243606
	30 May 1999	Second Round	#	Cults v Luncarty	Allan Park, Cults	misc243598
	30 May 1999	Second Round	#	Cumbernauld v Stonehaven Thistle	Cumbernauld Cricket Club Ground, Cumbernauld	misc243597
	30 May 1999	Second Round	#	Doune v Townhill	Moray Park, Doune	misc243596
	30 May 1999	Second Round		Ellon Gordon v Glasgow University Staff	Gordon Park, Ellon	misc243605a
	30 May 1999	Second Round	#	Fauldhouse Victoria v Perth Mayfield	Eastfield Park, Fauldhouse	misc243608
	30 May 1999	Second Round	#	Inverclyde v Kinloch	Gourock Park, Gourock	misc243601
	30 May 1999	Second Round		Keith v Drummond	Fife Park, Keith	misc243602a
	30 May 1999	Second Round		Manderston v St Andrews University Staff	Manderston, Duns	misc243610a
	30 May 1999	Second Round		Montrose v Westquarter and Redding	Union Park, Montrose	misc243611a
	30 May 1999	Second Round	#	Queen's Park (Scotland) v Dunlop	Queen's Park, Glasgow	misc243607
	30 May 1999	Second Round		Renfrew v Ardrossan	King George V Playing Fields, Renfrew	misc243604a
	30 May 1999	Second Round	#	Rouken Glen Young Men v Glendelvine	Rouken Glen Park, Glasgow	misc243600
	30 May 1999	Second Round	#	Ship Inn v Cramond	Elie Beach, Elie	misc243599
	30 May 1999	Second Round	#	Strathearn v Vale of Leven	Doo'cot Park No 1, Perth	misc243603
	20 Jun 1999	Third Round		Cramond v Queen's Park (Scotland)	Cramond Campus, Edinburgh	misc243616a
	20 Jun 1999	Third Round	#	Cults v Townhill	Allan Park, Cults	misc243613
	20 Jun 1999	Third Round	#	Ellon Gordon v Perth Mayfield	Gordon Park, Ellon	misc243612
	20 Jun 1999	Third Round		Glendelvine v Manderston	Glendelvine Cricket Club Ground, Spittalfield	misc243619a
	20 Jun 1999	Third Round	#	Kinloch v Keith	Lochee Park, Dundee	misc243615
	20 Jun 1999	Third Round		Montrose v Stonehaven Thistle	Union Park, Montrose	misc243617a
	20 Jun 1999	Third Round	#	Renfrew v Vale of Leven	King George V Playing Fields, Renfrew	misc243614
	20 Jun 1999	Third Round	#	Rossie Priory v Buckie	Rossie Priory, Inchture	misc243618
	04 Jul 1999	Quarter-Final	#	Cults v Glendelvine	Allan Park, Cults	misc243622
	04 Jul 1999	Quarter-Final	#	Ellon Gordon v Keith	Gordon Park, Ellon	misc243620
	04 Jul 1999	Quarter-Final	#	Renfrew v Cramond	King George V Playing Fields, Renfrew	misc243623
	04 Jul 1999	Quarter-Final	#	Rossie Priory v Stonehaven Thistle	Rossie Priory, Inchture	misc243621
	18 Jul 1999	Semi-Final	#	Cults v Keith	Allan Park, Cults	misc243624
	18 Jul 1999	Semi-Final	#	Renfrew v Stonehaven Thistle	King George V Playing Fields, Renfrew	misc243625
	08 Aug 1999	Final		Cults v Stonehaven Thistle	Lochside Park, Forfar	misc243626

The scorecards marked with a # are potted scores only.