24th May 1992	Whyte and Mackay Scottish Cup 1992	Preliminary Round Section 8	Royal High v Hillhead High School Former Pupils	East Barnton Avenue, Edinburgh	scocup474
	7th June 1992	Whyte and Mackay Scottish Cup 1992	Preliminary Round Section 8	Clydesdale v Hillhead High School Former Pupils	Titwood, Glasgow	scocup483
	5th July 1992	Whyte and Mackay Scottish Cup 1992	Preliminary Round Section 8	Hillhead High School Former Pupils v Kelso	Hughenden, Glasgow	scocup505
	16th May 1993	Whyte and Mackay Scottish Cup 1993	Preliminary Round Section 5	Drumpellier v Hillhead High School Former Pupils	Langloan, Coatbridge	scocup522
	20th June 1993	Whyte and Mackay Scottish Cup 1993	Preliminary Round Section 5	Ayr v Hillhead High School Former Pupils	Cambusdoon, Alloway	scocup535
	18th July 1993	Whyte and Mackay Scottish Cup 1993	Preliminary Round Section 5	Hillhead High School Former Pupils v Carlton	Hughenden, Glasgow	scocup560
	14th May 1995	Whyte and Mackay Scottish Cup 1995	Preliminary Round Section 4	Carlton v Hillhead High School Former Pupils	Grange Loan, Edinburgh	scocup630
	28th May 1995	Whyte and Mackay Scottish Cup 1995	Preliminary Round Section 4	Hillhead High School Former Pupils v Aberdeenshire	Hughenden, Glasgow	scocup649
	11th June 1995	Whyte and Mackay Scottish Cup 1995	Preliminary Round Section 4	Ayr v Hillhead High School Former Pupils	Cambusdoon, Alloway	scocup652
	25th June 1995	Whyte and Mackay Scottish Cup 1995	Preliminary Round Section 4	Ayrshire v Hillhead High School Former Pupils	Henry Thow Oval, Prestwick	scocup666
	9th July 1995	Whyte and Mackay Scottish Cup 1995	Preliminary Round Section 4	Hillhead High School Former Pupils v Inverurie	Hughenden, Glasgow	scocup683
	11th May 1997	Whyte and Mackay Scottish Cup 1997	Preliminary Round Section 1	Ferguslie v Hillhead High School Former Pupils	Meikleriggs, Paisley	scocup763
	18th May 1997	Whyte and Mackay Scottish Cup 1997	Preliminary Round Section 1	Hillhead High School Former Pupils v Strathmore	Hughenden, Glasgow	scocup775
	1st June 1997	Whyte and Mackay Scottish Cup 1997	Preliminary Round Section 1	Aberdeenshire v Hillhead High School Former Pupils	Mannofield Park, Aberdeen	scocup782
	15th June 1997	Whyte and Mackay Scottish Cup 1997	Preliminary Round Section 1	Hillhead High School Former Pupils v Stirling County	Hughenden, Glasgow	scocup800
	29th June 1997	Whyte and Mackay Scottish Cup 1997	Preliminary Round Section 1	Gala v Hillhead High School Former Pupils	Meigle Park, Galashiels	scocup812
	17th May 1998	Whyte and Mackay Scottish Cup 1998	Preliminary Round Section 2	Aberdeenshire v Hillhead High School Former Pupils	Mannofield Park, Aberdeen	scocup825
	31st May 1998	Whyte and Mackay Scottish Cup 1998	Preliminary Round Section 2	Poloc v Hillhead High School Former Pupils	Shawholm, Glasgow	scocup844
	14th June 1998	Whyte and Mackay Scottish Cup 1998	Preliminary Round Section 2	Stoneywood-Dyce v Hillhead High School Former Pupils	People's Park, Aberdeen	scocup859
	21st June 1998	Whyte and Mackay Scottish Cup 1998	Preliminary Round Section 2	West Lothian v Hillhead High School Former Pupils	Boghall, Linlithgow	scocup872
	28th June 1998	Whyte and Mackay Scottish Cup 1998	Preliminary Round Section 2	Gala v Hillhead High School Former Pupils	Meigle Park, Galashiels	scocup877
	30th May 1999	Scottish Cup 1999	Preliminary Round Section 3	Heriot's v Hillhead High School Former Pupils	Goldenacre, Edinburgh	scocup896a
	13th June 1999	Scottish Cup 1999	Preliminary Round Section 3	Hillhead High School Former Pupils v Carlton	Hughenden, Glasgow	scocup902c
	20th June 1999	Scottish Cup 1999	Preliminary Round Section 3	Glenrothes v Hillhead High School Former Pupils	Riverside Park, Glenrothes	scocup908
	27th June 1999	Scottish Cup 1999	Preliminary Round Section 3	Hillhead High School Former Pupils v St Michael's	Hughenden, Glasgow	scocup916
	4th July 1999	Scottish Cup 1999	Preliminary Round Section 3	Hillhead High School Former Pupils v Ayr	Hughenden, Glasgow	scocup920
	7th May 2000	Scottish Cup 2000	Section Three	West of Scotland v Hillhead High School Former Pupils	Hamilton Crescent, Glasgow	scocup941
	21st May 2000	Scottish Cup 2000	Section Three	Greenock v Hillhead High School Former Pupils	Glenpark, Greenock	scocup949
	4th June 2000	Scottish Cup 2000	Section Three	Watsonians v Hillhead High School Former Pupils	Myreside, Edinburgh	scocup961a
	18th June 2000	Scottish Cup 2000	Section Three	Hillhead High School Former Pupils v Dunfermline	Hughenden, Glasgow	scocup968
	2nd July 2000	Scottish Cup 2000	Section Three	Prestwick v Hillhead High School Former Pupils	Henry Thow Oval, Prestwick	scocup982
	6th May 2001	Scottish Cup 2001	Section 1	Hillhead High School Former Pupils v West of Scotland	Hughenden, Glasgow	scocup1000
	13th May 2001	Scottish Cup 2001	Section 1	Hillhead High School Former Pupils v Aberdeenshire	Hughenden, Glasgow	scocup1012
	27th May 2001	Scottish Cup 2001	Section 1	Drumpellier v Hillhead High School Former Pupils	Langloan, Coatbridge	scocup1019
	3rd June 2001	Scottish Cup 2001	Section 1	Falkland v Hillhead High School Former Pupils	Scroggie Park, Falkland	scocup1033
	10th June 2001	Scottish Cup 2001	Section 1	Clydesdale v Hillhead High School Former Pupils	Titwood, Glasgow	scocup1044
	15th June 2003	Coronel Scottish Cup 2003	First Round	Perthshire v Hillhead High School Former Pupils	North Inch, Perth	scocup1110
	22nd June 2003	Coronel Scottish Cup 2003	Second Round	Hillhead High School Former Pupils v Dunfermline	Hughenden, Glasgow	scocup1118
	30th May 2004	Coronel Scottish Cup 2004	First Round	Hillhead High School Former Pupils v Stirling County	Hughenden, Glasgow	scocup1139
	15th May 2005	Coronel Scottish Cup 2005	First Round	Clydesdale v Hillhead High School Former Pupils	Titwood, Glasgow	scocup1165
	29th May 2011	Scottish Cup 2011	First Round	Hillhead High School Former Pupils v Stenhousemuir	Hughenden, Glasgow	scocup1352b

37 fixtures and matches, excluding 4 abandoned or cancelled matches