25th May 1969	The Cricketer Cup 1969	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup44
	15th June 1969	The Cricketer Cup 1969	Second Round	Stowe Templars v Old Cholmeleians	Stowe School Ground, Stowe	crcup58
	31st May 1970	The Cricketer Cup 1970	First Round	Radley Rangers v Old Cholmeleians	Radley College Bigside Ground, Abingdon	crcup81
	30th May 1971	The Cricketer Cup 1971	First Round	Old Cholmeleians v Felsted Robins	Highgate School Ground, Highgate	crcup105
	28th May 1972	The Cricketer Cup 1972	First Round	Old Cholmeleians v St Edward's Martyrs	Hendon Wood Lane, Mill Hill	crcup140
	27th May 1973	The Cricketer Cup 1973	First Round	Repton Pilgrims v Old Cholmeleians	Repton School Ground, Repton	crcup176
	17th June 1973	The Cricketer Cup 1973	Second Round	Old Blundellians v Old Cholmeleians	Blundell's School, Tiverton	crcup182
	2nd June 1974	The Cricketer Cup 1974	First Round	Old Cholmeleians v Old Brightonians	Highgate School Ground, Highgate	crcup201
	1st June 1975	The Cricketer Cup 1975	First Round	Old Malvernians v Old Cholmeleians	Malvern College Ground, Malvern	crcup236
	30th May 1976	The Cricketer Cup 1976	First Round	Repton Pilgrims v Old Cholmeleians	Repton School Ground, Repton	crcup270
	5th June 1977	The Cricketer Cup 1977	First Round	Old Cholmeleians v Charterhouse Friars	Highgate School Ground, Highgate	crcup299
	4th June 1978	The Cricketer Cup 1978	First Round	Rugby Meteors v Old Cholmeleians	Rugby School Ground, Rugby	crcup332
	18th June 1978	The Cricketer Cup 1978	Second Round	Old Cholmeleians v Old Wellingtonians	Highgate School Ground, Highgate	crcup339
	3rd June 1979	The Cricketer Cup 1979	First Round	Old Whitgiftians v Old Cholmeleians	Whitgift School, Croydon	crcup361
	1st June 1980	The Cricketer Cup 1980	First Round	Old Cholmeleians v Downside Wanderers	Highgate School Ground, Highgate	crcup389
	15th June 1980	The Cricketer Cup 1980	Second Round	Old Cholmeleians v Old Wykehamists	Highgate School Ground, Highgate	crcup399
	31st May 1981	The Cricketer Cup 1981	First Round	Harrow Wanderers v Old Cholmeleians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup418
	30th May 1982	The Cricketer Cup 1982	First Round	Bradfield Waifs v Old Cholmeleians	Bradfield College, Reading	crcup447
	13th June 1982	The Cricketer Cup 1982	Second Round	Harrow Wanderers v Old Cholmeleians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup466
	5th June 1983	The Cricketer Cup 1983	First Round	Stowe Templars v Old Cholmeleians	Stowe School Ground, Stowe	crcup493
	12th June 1983	The Cricketer Cup 1983	Second Round	Old Cholmeleians v St Edward's Martyrs	Highgate School Ground, Highgate	crcup497
	3rd June 1984	The Cricketer Cup 1984	First Round	Old Merchant Taylors v Old Cholmeleians	Durrants Sports Ground, Croxley Green	crcup516
	2nd June 1985	The Cricketer Cup 1985	First Round	Old Cholmeleians v Rugby Meteors	Highgate School Ground, Highgate	crcup547
	30th June 1985	The Cricketer Cup 1985	Second Round	Old Cliftonians v Old Cholmeleians	Clifton College Close Ground, Clifton	crcup565
	1st June 1986	The Cricketer Cup 1986	First Round	Uppingham Rovers v Old Cholmeleians	Upper Field, Uppingham School	crcup588
	22nd June 1986	The Cricketer Cup 1986	Second Round	Felsted Robins v Old Cholmeleians	Felsted School Ground, Dunmow	crcup589
	31st May 1987	The Cricketer Cup 1987	First Round	Lancing Rovers v Old Cholmeleians	Lancing College Ground, Lancing	crcup607
	29th May 1988	The Cricketer Cup 1988	First Round	Shrewsbury Saracens v Old Cholmeleians	Shrewsbury School, Shrewsbury	crcup649
	4th June 1989	The Cricketer Cup 1989	First Round	Old Cholmeleians v Repton Pilgrims	Highgate School Ground, Highgate	crcup673
	3rd June 1990	The Cricketer Cup 1990	First Round	Eton Ramblers v Old Cholmeleians	Upper Club, Eton College	crcup700
	2nd June 1991	The Cricketer Cup 1991	First Round	Old Cholmeleians v Repton Pilgrims	Highgate School Ground, Highgate	crcup737
	31st May 1992	The Cricketer Cup 1992	First Round	Harrow Wanderers v Old Cholmeleians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup765
	30th May 1993	The Cricketer Cup 1993	First Round	Old Brightonians v Old Cholmeleians	Brighton College Ground, Brighton	crcup797
	29th May 1994	The Cricketer Cup 1994	First Round	Old Blundellians v Old Cholmeleians	Blundell's School, Tiverton	crcup828
	11th June 1995	The Cricketer Cup 1995	First Round	Charterhouse Friars v Old Cholmeleians	Charterhouse School, Godalming	crcup866
	2nd June 1996	The Cricketer Cup 1996	First Round	Old Cholmeleians v Rugby Meteors	Highgate School Ground, Highgate	crcup893
	23rd June 1996	The Cricketer Cup 1996	Second Round	Old Cholmeleians v Uppingham Rovers	Highgate School Ground, Highgate	crcup908
	1st June 1997	The Cricketer Cup 1997	First Round	Old Alleynians v Old Cholmeleians	Dulwich College Ground, Dulwich	crcup924
	29th June 1997	The Cricketer Cup 1997	Second Round	Old Tonbridgians v Old Cholmeleians	Tonbridge School Ground, Tonbridge	crcup938
	31st May 1998	The Cricketer Cup 1998	First Round	Old Cholmeleians v St Edward's Martyrs	Highgate School Ground, Highgate	crcup954
	21st June 1998	The Cricketer Cup 1998	Second Round	Old Cholmeleians v Felsted Robins	Highgate School Ground, Highgate	crcup970
	30th May 1999	The Cricketer Cup 1999	First Round	Old Cholmeleians v Old Merchant Taylors	Highgate School Ground, Highgate	crcup985
	18th June 2000	The Cricketer Cup 2000	First Round	Uppingham Rovers v Old Cholmeleians	Middle Field Pitch 1, Uppingham School	crcup1027
	10th June 2001	The Cricketer Cup 2001	First Round	Old Cholmeleians v Eton Ramblers	Highgate School Ground, Highgate	crcup1048
	2nd June 2002	The Cricketer Cup 2002	First Round	Old Cholmeleians v Marlborough Blues	Highgate School Ground, Highgate	crcup1080
	16th June 2002	The Cricketer Cup 2002	Second Round	Old Cholmeleians v Shrewsbury Saracens	Highgate School Ground, Highgate	crcup1089
	15th June 2003	The Cricketer Cup 2003	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup1110
	13th June 2004	The Cricketer Cup 2004	First Round	Old Cholmeleians v Old Malvernians	Highgate School Ground, Highgate	crcup1138
	12th June 2005	The Cricketer Cup 2005	First Round	Uppingham Rovers v Old Cholmeleians	Middle Field Pitch 1, Uppingham School	crcup1179
	11th June 2006	The Cricketer Cup 2006	First Round	Old Cholmeleians v Old Malvernians	Highgate School Ground, Highgate	crcup1200
	10th June 2007	The Cricketer Cup 2007	First Round	Old Cholmeleians v Old Amplefordians	Highgate School Ground, Highgate	crcup1230
	24th June 2007	The Cricketer Cup 2007	Second Round	Old Cholmeleians v Old Cranleighans	Highgate School Ground, Highgate	crcup1240b
	8th July 2007	The Cricketer Cup 2007	Quarter-Final	Old Cholmeleians v Old Wellingtonians	Highgate School Ground, Highgate	crcup1245
	15th June 2008	The Cricketer Cup 2008	First Round	Old Whitgiftians v Old Cholmeleians	Whitgift School, Croydon	crcup1261
	14th June 2009	The Cricketer Cup 2009	First Round	Old Cholmeleians v Old Merchant Taylors	Highgate School Ground, Highgate	crcup1287
	13th June 2010	The Cricketer Cup 2010	First Round	Old Cholmeleians v Old Amplefordians	Highgate School Ground, Highgate	crcup1320
	4th July 2010	The Cricketer Cup 2010	Second Round	Old Wellingtonians v Old Cholmeleians	Wellington College, Crowthorne	crcup1335
	12th June 2011	The Cricketer Cup 2011	First Round	Old Eastbournians v Old Cholmeleians	Eastbourne College Ground, Eastbourne	crcup1344
	17th June 2012	The Cricketer Cup 2012	First Round	Marlborough Blues v Old Cholmeleians	Marlborough College Ground, Marlborough	crcup1378
	16th June 2013	The Cricketer Cup 2013	First Round	Stowe Templars v Old Cholmeleians	Stowe School Ground, Stowe	crcup1417
	15th June 2014	The Cricketer Cup 2014	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup1437
	14th June 2015	The Cricketer Cup 2015	First Round	Sherborne Pilgrims v Old Cholmeleians	Sherborne School, Sherborne	crcup1476
	12th June 2016	The Cricketer Cup 2016	First Round	Old Cholmeleians v Downside Wanderers	Tivoli Road, Hornsey	crcup1498
	11th June 2017	The Cricketer Cup 2017	First Round	Old Hurst Johnians v Old Cholmeleians	Hurstpierpoint College Ground, Hurstpierpoint	crcup1534
	25th June 2017	The Cricketer Cup 2017	Second Round	Old Cholmeleians v Marlborough Blues	Harman Drive, Brondesbury	crcup1544
	17th June 2018	The Cricketer Cup 2018	First Round	Old Cholmeleians v Uppingham Rovers	Highgate School Ground, Highgate	crcup1561
	16th June 2019	The Cricketer Cup 2019	First Round	St Edward's Martyrs v Old Cholmeleians	St Edward's School Ground, Oxford	crcup1598
	14th June 2020	The Cricketer Cup 2020	First Round	Old Cholmeleians v Haileybury Hermits	Highgate School Ground, Highgate	crcup1616i
	13th June 2021	The Cricketer Cup 2021	First Round	Harrow Wanderers v Old Cholmeleians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup1621
	12th June 2022	The Cricketer Cup 2022	First Round	Radley Rangers v Old Cholmeleians	Radley College Bigside Ground, Abingdon	crcup1667
	11th June 2023	The Cricketer Cup 2023	First Round	St Edward's Martyrs v Old Cholmeleians	St Edward's School Ground, Oxford	crcup1701
	9th June 2024	The Cricketer Cup 2024	First Round	Old Brightonians v Old Cholmeleians	Brighton College Ground, Brighton	crcup1728
	8th June 2025	The Cricketer Cup 2025	First Round	Repton Pilgrims v Old Cholmeleians	Repton School Ground, Repton	crcup1769

71 fixtures and matches, excluding 2 abandoned or cancelled matches

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