25th May 1969	The Cricketer Cup 1969	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup44
	31st May 1970	The Cricketer Cup 1970	First Round	Marlborough Blues v Old Cheltonians	Marlborough College Ground, Marlborough	crcup72
	30th May 1971	The Cricketer Cup 1971	First Round	Old Cheltonians v Harrow Wanderers	College Ground, Cheltenham	crcup104
	28th May 1972	The Cricketer Cup 1972	First Round	Old Cheltonians v Old Alleynians	College Ground, Cheltenham	crcup139
	27th May 1973	The Cricketer Cup 1973	First Round	Radley Rangers v Old Cheltonians	Radley College Bigside Ground, Abingdon	crcup175
	2nd June 1974	The Cricketer Cup 1974	First Round	Old Cheltonians v Old Amplefordians	College Ground, Cheltenham	crcup200
	16th June 1974	The Cricketer Cup 1974	Second Round	Old Cheltonians v Old Alleynians	College Ground, Cheltenham	crcup213
	1st June 1975	The Cricketer Cup 1975	First Round	Haileybury Hermits v Old Cheltonians	Haileybury College Ground, Hertford	crcup229
	30th May 1976	The Cricketer Cup 1976	First Round	Marlborough Blues v Old Cheltonians	Marlborough College Ground, Marlborough	crcup262
	5th June 1977	The Cricketer Cup 1977	First Round	Haileybury Hermits v Old Cheltonians	Haileybury College Ground, Hertford	crcup292
	4th June 1978	The Cricketer Cup 1978	First Round	Old Cliftonians v Old Cheltonians	Clifton College Close Ground, Clifton	crcup325
	18th June 1978	The Cricketer Cup 1978	Second Round	Old Cheltonians v Radley Rangers	College Ground, Cheltenham	crcup338
	3rd June 1979	The Cricketer Cup 1979	First Round	Old Cheltonians v Old Alleynians	College Ground, Cheltenham	crcup355
	1st June 1980	The Cricketer Cup 1980	First Round	Old Cheltonians v Old Wellingtonians	College Ground, Cheltenham	crcup388
	31st May 1981	The Cricketer Cup 1981	First Round	Old Cheltonians v Old Tonbridgians	College Ground, Cheltenham	crcup423
	30th May 1982	The Cricketer Cup 1982	First Round	Old Cheltonians v Felsted Robins	Felsted School Ground, Dunmow	crcup454
	13th June 1982	The Cricketer Cup 1982	Second Round	Old Cliftonians v Old Cheltonians	Clifton College Close Ground, Clifton	crcup468
	29th May 1983	The Cricketer Cup 1983	First Round	Sherborne Pilgrims v Old Cheltonians	Sherborne School, Sherborne	crcup487
	3rd June 1984	The Cricketer Cup 1984	First Round	Charterhouse Friars v Old Cheltonians	Charterhouse School, Godalming	crcup509
	2nd June 1985	The Cricketer Cup 1985	First Round	Old Wykehamists v Old Cheltonians	Ridding Field, Winchester	crcup552
	1st June 1986	The Cricketer Cup 1986	First Round	Old Wykehamists v Old Cheltonians	Ridding Field, Winchester	crcup583
	31st May 1987	The Cricketer Cup 1987	First Round	Old Cheltonians v Repton Pilgrims	College Ground, Cheltenham	crcup611
	29th May 1988	The Cricketer Cup 1988	First Round	Old Amplefordians v Old Cheltonians	Ampleforth College, Ampleforth	crcup641
	4th June 1989	The Cricketer Cup 1989	First Round	Old Wellingtonians v Old Cheltonians	Wellington College, Crowthorne	crcup676
	3rd June 1990	The Cricketer Cup 1990	First Round	Harrow Wanderers v Old Cheltonians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup701
	2nd June 1991	The Cricketer Cup 1991	First Round	Old Cheltonians v Old Tonbridgians	College Ground, Cheltenham	crcup736
	31st May 1992	The Cricketer Cup 1992	First Round	Haileybury Hermits v Old Cheltonians	Haileybury College Ground, Hertford	crcup764
	6th June 1993	The Cricketer Cup 1993	First Round	Old Wykehamists v Old Cheltonians	Ridding Field, Winchester	crcup807
	20th June 1993	The Cricketer Cup 1993	Second Round	Old Cheltonians v Marlborough Blues	College Ground, Cheltenham	crcup812
	29th May 1994	The Cricketer Cup 1994	First Round	Haileybury Hermits v Old Cheltonians	Haileybury College Ground, Hertford	crcup825
	4th June 1995	The Cricketer Cup 1995	First Round	Harrow Wanderers v Old Cheltonians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup858
	25th June 1995	The Cricketer Cup 1995	Second Round	Old Cheltonians v Old Wellingtonians	College Ground, Cheltenham	crcup874
	2nd June 1996	The Cricketer Cup 1996	First Round	Bradfield Waifs v Old Cheltonians	Bradfield College, Reading	crcup887
	1st June 1997	The Cricketer Cup 1997	First Round	Lancing Rovers v Old Cheltonians	Lancing College Ground, Lancing	crcup923
	22nd June 1997	The Cricketer Cup 1997	Second Round	Old Cheltonians v Harrow Wanderers	College Ground, Cheltenham	crcup935
	31st May 1998	The Cricketer Cup 1998	First Round	Old Merchant Taylors v Old Cheltonians	Durrants Sports Ground, Croxley Green	crcup957
	30th May 1999	The Cricketer Cup 1999	First Round	Old Brightonians v Old Cheltonians	Brighton College Ground, Brighton	crcup984
	18th June 2000	The Cricketer Cup 2000	First Round	Lancing Rovers v Old Cheltonians	Lancing College Ground, Lancing	crcup1014
	10th June 2001	The Cricketer Cup 2001	First Round	Old Cheltonians v Old Amplefordians	College Ground, Cheltenham	crcup1047
	24th June 2001	The Cricketer Cup 2001	Second Round	Oundle Rovers v Old Cheltonians	Oundle School Ground, Oundle	crcup1065
	2nd June 2002	The Cricketer Cup 2002	First Round	Old Cheltonians v Rugby Meteors	College Ground, Cheltenham	crcup1079
	16th June 2002	The Cricketer Cup 2002	Second Round	Old Wellingtonians v Old Cheltonians	Wellington College, Crowthorne	crcup1091
	15th June 2003	The Cricketer Cup 2003	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup1110
	29th June 2003	The Cricketer Cup 2003	Second Round	Oundle Rovers v Old Cheltonians	Oundle School Ground, Oundle	crcup1124
	13th June 2004	The Cricketer Cup 2004	First Round	Charterhouse Friars v Old Cheltonians	Charterhouse School, Godalming	crcup1134
	12th June 2005	The Cricketer Cup 2005	First Round	Eton Ramblers v Old Cheltonians	Upper Club, Eton College	crcup1165
	11th June 2006	The Cricketer Cup 2006	First Round	Old Cheltonians v Shrewsbury Saracens	College Ground, Cheltenham	crcup1199
	25th June 2006	The Cricketer Cup 2006	Second Round	Eton Ramblers v Old Cheltonians	Upper Club, Eton College	crcup1211
	10th June 2007	The Cricketer Cup 2007	First Round	Old Cheltonians v Old Alleynians	College Ground, Cheltenham	crcup1229
	15th June 2008	The Cricketer Cup 2008	First Round	Old Wellingtonians v Old Cheltonians	Wellington College, Crowthorne	crcup1259
	29th June 2008	The Cricketer Cup 2008	Second Round	Old Cheltonians v Harrow Wanderers	College Ground, Cheltenham	crcup1270
	13th July 2008	The Cricketer Cup 2008	Quarter-Final	Old Cheltonians v Old Cranleighans	College Ground, Cheltenham	crcup1276
	14th June 2009	The Cricketer Cup 2009	First Round	Old Cliftonians v Old Cheltonians	Clifton College Close Ground, Clifton	crcup1288
	13th June 2010	The Cricketer Cup 2010	First Round	Old Cheltonians v Felsted Robins	College Ground, Cheltenham	crcup1319
	4th July 2010	The Cricketer Cup 2010	Second Round	Old Cheltonians v Oundle Rovers	College Ground, Cheltenham	crcup1334
	19th June 2011	The Cricketer Cup 2011	First Round	Old Cheltonians v Haileybury Hermits	College Ground, Cheltenham	crcup1349
	26th June 2011	The Cricketer Cup 2011	Second Round	Old Cheltonians v Uppingham Rovers	College Ground, Cheltenham	crcup1360
	10th July 2011	The Cricketer Cup 2011	Quarter-Final	Old Malvernians v Old Cheltonians	Malvern College Ground, Malvern	crcup1367
	17th June 2012	The Cricketer Cup 2012	First Round	Repton Pilgrims v Old Cheltonians	Repton School Ground, Repton	crcup1383
	1st July 2012	The Cricketer Cup 2012	Second Round	Harrow Wanderers v Old Cheltonians	Harrow School Cricket Ground, Harrow-on-the-Hill	crcup1390
	16th June 2013	The Cricketer Cup 2013	First Round	Old Cheltonians v Old Alleynians	College Ground, Cheltenham	crcup1409
	30th June 2013	The Cricketer Cup 2013	Second Round	Old Cheltonians v Eton Ramblers	College Ground, Cheltenham	crcup1419
	14th July 2013	The Cricketer Cup 2013	Quarter-Final	Charterhouse Friars v Old Cheltonians	Charterhouse School, Godalming	crcup1426
	15th June 2014	The Cricketer Cup 2014	First Round	Old Cheltonians v Old Cholmeleians	College Ground, Cheltenham	crcup1437
	29th June 2014	The Cricketer Cup 2014	Second Round	Old Cheltonians v Harrow Wanderers	College Ground, Cheltenham	crcup1449
	13th July 2014	The Cricketer Cup 2014	Quarter-Final	Old Cranleighans v Old Cheltonians	Jubilee, Cranleigh School	crcup1458
	14th June 2015	The Cricketer Cup 2015	First Round	Old Cheltonians v Old Merchant Taylors	College Ground, Cheltenham	crcup1470
	28th June 2015	The Cricketer Cup 2015	Second Round	Stowe Templars v Old Cheltonians	Stowe School Ground, Stowe	crcup1486
	12th July 2015	The Cricketer Cup 2015	Quarter-Final	Old Wellingtonians v Old Cheltonians	Wellington College, Crowthorne	crcup1489
	12th June 2016	The Cricketer Cup 2016	First Round	Old Tonbridgians v Old Cheltonians	Tonbridge School Ground, Tonbridge	crcup1503
	11th June 2017	The Cricketer Cup 2017	First Round	Marlborough Blues v Old Cheltonians	Marlborough College Ground, Marlborough	crcup1529
	17th June 2018	The Cricketer Cup 2018	First Round	Old Cheltonians v Sherborne Pilgrims	College Ground, Cheltenham	crcup1560
	16th June 2019	The Cricketer Cup 2019	First Round	Old Cheltonians v Oundle Rovers	College Ground, Cheltenham	crcup1591
	14th June 2020	The Cricketer Cup 2020	First Round	Old Cheltonians v Bradfield Waifs	College Ground, Cheltenham	crcup1616h
	13th June 2021	The Cricketer Cup 2021	First Round	Downside Wanderers v Old Cheltonians	Downside School, Stratton-on-the-Fosse	crcup1619
	27th June 2021	The Cricketer Cup 2021	Second Round	Haileybury Hermits v Old Cheltonians	Haileybury College Ground, Hertford	crcup1637
	11th July 2021	The Cricketer Cup 2021	Quarter-Final	Old Malvernians v Old Cheltonians	Malvern College Ground, Malvern	crcup1645a
	12th June 2022	The Cricketer Cup 2022	First Round	Old Amplefordians v Old Cheltonians	Ampleforth College, Ampleforth	crcup1660
	26th June 2022	The Cricketer Cup 2022	Second Round	Old Merchant Taylors v Old Cheltonians	Merchant Taylors' School Ground, Northwood	crcup1673
	10th July 2022	The Cricketer Cup 2022	Quarter-Final	Shrewsbury Saracens v Old Cheltonians	Shrewsbury School, Shrewsbury	crcup1681
	24th July 2022	The Cricketer Cup 2022	Semi-Final	Old Cheltonians v Bradfield Waifs	College Ground, Cheltenham	crcup1682
	14th May 2023	The Cricketer Cup 2023	Preliminary Round	Old Cheltonians v Haileybury Hermits	College Ground, Cheltenham	crcup1685
	11th June 2023	The Cricketer Cup 2023	First Round	Old Cheltonians v Marlborough Blues	College Ground, Cheltenham	crcup1690
	25th June 2023	The Cricketer Cup 2023	Second Round	Old Millfieldians v Old Cheltonians	Millfield School, Street	crcup1706
	9th June 2024	The Cricketer Cup 2024	First Round	Old Cheltonians v Old Cliftonians	College Ground, Cheltenham	crcup1729
	30th June 2024	The Cricketer Cup 2024	Second Round	Old Amplefordians v Old Cheltonians	Ampleforth College, Ampleforth	crcup1739
	14th July 2024	The Cricketer Cup 2024	Quarter-Final	Charterhouse Friars v Old Cheltonians	Charterhouse School, Godalming	crcup1746
	8th June 2025	The Cricketer Cup 2025	First Round	Old Wykehamists v Old Cheltonians	Ridding Field, Winchester	crcup1767

87 fixtures and matches, excluding 1 abandoned or cancelled matches

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