| Extras |
| 47 | Old Brightonians v Old Cheltonians | Brighton College Ground, Brighton | 1999 |
| 42 | Rugby Meteors v Old Cheltonians | College Ground, Cheltenham | 2002 |
| 39 | Harrow Wanderers v Old Cheltonians | Harrow School Cricket Ground, Harrow-on-the-Hill | 2012 |
| 37 | Uppingham Rovers v Old Cheltonians | College Ground, Cheltenham | 2011 |
| 36 | Oundle Rovers v Old Cheltonians | Oundle School Ground, Oundle | 2003 |
| 34 | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | 1992 |
| 33 | Repton Pilgrims v Old Cheltonians | Repton School Ground, Repton | 2012 |
| 30 | Old Alleynians v Old Cheltonians | College Ground, Cheltenham | 2007 |
| 29 | Old Amplefordians v Old Cheltonians | Ampleforth College, Ampleforth | 2022 |
| 28 | Old Malvernians v Old Cheltonians | Malvern College Ground, Malvern | 2011 |
| 27 | Old Merchant Taylors v Old Cheltonians | College Ground, Cheltenham | 2015 |
| 27 | Marlborough Blues v Old Cheltonians | College Ground, Cheltenham | 2023 |
| 26 | Marlborough Blues v Old Cheltonians | College Ground, Cheltenham | 1993 |
| 26 | Lancing Rovers v Old Cheltonians | Lancing College Ground, Lancing | 2000 |
| 26 | Charterhouse Friars v Old Cheltonians | Charterhouse School, Godalming | 2004 |
| 26 | Felsted Robins v Old Cheltonians | College Ground, Cheltenham | 2010 |
| 26 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 2025 |
| 25 | Old Tonbridgians v Old Cheltonians | College Ground, Cheltenham | 1991 |
| 25 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2003 |
| 25 | Harrow Wanderers v Old Cheltonians | College Ground, Cheltenham | 2014 |
| 24 | Lancing Rovers v Old Cheltonians | Lancing College Ground, Lancing | 1997 |
| 22 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1993 |
| 22 | Old Merchant Taylors v Old Cheltonians | Durrants Sports Ground, Croxley Green | 1998 |
| 22 | Oundle Rovers v Old Cheltonians | Oundle School Ground, Oundle | 2001 |
| 22 | Old Merchant Taylors v Old Cheltonians | Merchant Taylors' School Ground, Northwood | 2022 |
| 22 | Shrewsbury Saracens v Old Cheltonians | Shrewsbury School, Shrewsbury | 2022 |
| 20 | Harrow Wanderers v Old Cheltonians | Harrow School Cricket Ground, Harrow-on-the-Hill | 1995 |
| 20 | Harrow Wanderers v Old Cheltonians | College Ground, Cheltenham | 1997 |
| 20 | Old Amplefordians v Old Cheltonians | College Ground, Cheltenham | 2001 |
| 20 | Haileybury Hermits v Old Cheltonians | College Ground, Cheltenham | 2023 |
