| 6 | Old Cheltonians v Oundle Rovers | Oundle School Ground, Oundle | 2003 |
| 5 | Old Cheltonians v Marlborough Blues | Marlborough College Ground, Marlborough | 1976 |
| 5 | Old Cheltonians v Charterhouse Friars | Charterhouse School, Godalming | 1984 |
| 5 | Old Cheltonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1990 |
| 5 | Old Cheltonians v Haileybury Hermits | Haileybury College Ground, Hertford | 1994 |
| 5 | Old Cheltonians v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1998 |
| 4 | Old Cheltonians v Sherborne Pilgrims | Sherborne School, Sherborne | 1983 |
| 4 | Old Cheltonians v Lancing Rovers | Lancing College Ground, Lancing | 1997 |
| 4 | Old Cheltonians v Old Cliftonians | Clifton College Close Ground, Clifton | 2009 |
| 4 | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | 2014 |
| 4 | Old Cheltonians v Stowe Templars | Stowe School Ground, Stowe | 2015 |
| 4 | Old Cheltonians v Bradfield Waifs | College Ground, Cheltenham | 2022 |
| 4 | Old Cheltonians v Old Millfieldians | Millfield School, Street | 2025 |
| 3 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1974 |
| 3 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1979 |
| 3 | Old Cheltonians v Old Tonbridgians | College Ground, Cheltenham | 1991 |
| 3 | Old Cheltonians v Haileybury Hermits | Haileybury College Ground, Hertford | 1992 |
| 3 | Old Cheltonians v Old Amplefordians | College Ground, Cheltenham | 2001 |
| 3 | Old Cheltonians v Old Wellingtonians | Wellington College, Crowthorne | 2002 |
| 3 | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | 2003 |
| 3 | Old Cheltonians v Charterhouse Friars | Charterhouse School, Godalming | 2004 |
| 3 | Old Cheltonians v Eton Ramblers | Upper Club, Eton College | 2005 |
| 3 | Old Cheltonians v Old Wellingtonians | Wellington College, Crowthorne | 2008 |
| 3 | Old Cheltonians v Oundle Rovers | College Ground, Cheltenham | 2010 |
| 3 | Old Cheltonians v Old Wellingtonians | Wellington College, Crowthorne | 2015 |
| 3 | Old Cheltonians v Old Cliftonians | College Ground, Cheltenham | 2024 |
| 3 | Old Cheltonians v Old Wykehamists | Ridding Field, Winchester | 2025 |
| 2 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1972 |
| 2 | Old Cheltonians v Radley Rangers | Radley College Bigside Ground, Abingdon | 1973 |
| 2 | Old Cheltonians v Old Cliftonians | Clifton College Close Ground, Clifton | 1982 |
| 2 | Old Cheltonians v Old Wykehamists | Ridding Field, Winchester | 1985 |
| 2 | Old Cheltonians v Repton Pilgrims | College Ground, Cheltenham | 1987 |
| 2 | Old Cheltonians v Old Wykehamists | Ridding Field, Winchester | 1993 |
| 2 | Old Cheltonians v Bradfield Waifs | Bradfield College, Reading | 1996 |
| 2 | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | 1997 |
| 2 | Old Cheltonians v Old Brightonians | Brighton College Ground, Brighton | 1999 |
| 2 | Old Cheltonians v Lancing Rovers | Lancing College Ground, Lancing | 2000 |
| 2 | Old Cheltonians v Oundle Rovers | Oundle School Ground, Oundle | 2001 |
| 2 | Old Cheltonians v Eton Ramblers | Upper Club, Eton College | 2006 |
| 2 | Old Cheltonians v Old Malvernians | Malvern College Ground, Malvern | 2011 |
| 2 | Old Cheltonians v Repton Pilgrims | Repton School Ground, Repton | 2012 |
| 2 | Old Cheltonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2012 |
| 2 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 2013 |
| 2 | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | 2014 |
| 2 | Old Cheltonians v Sherborne Pilgrims | College Ground, Cheltenham | 2018 |
| 2 | Old Cheltonians v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 2021 |
| 2 | Old Cheltonians v Old Amplefordians | Ampleforth College, Ampleforth | 2022 |
| 2 | Old Cheltonians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 2022 |
| 2 | Old Cheltonians v Old Millfieldians | Millfield School, Street | 2023 |
