| Extras |
| 57 | Old Cholmeleians v Old Amplefordians | Highgate School Ground, Highgate | 2007 |
| 36 | Old Cholmeleians v Old Hurst Johnians | Hurstpierpoint College Ground, Hurstpierpoint | 2017 |
| 34 | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | 2009 |
| 33 | Old Cholmeleians v Sherborne Pilgrims | Sherborne School, Sherborne | 2015 |
| 31 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1982 |
| 31 | Old Cholmeleians v Eton Ramblers | Highgate School Ground, Highgate | 2001 |
| 29 | Old Cholmeleians v Old Blundellians | Blundell's School, Tiverton | 1994 |
| 28 | Old Cholmeleians v Rugby Meteors | Highgate School Ground, Highgate | 1985 |
| 27 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1992 |
| 27 | Old Cholmeleians v Old Brightonians | Brighton College Ground, Brighton | 1993 |
| 26 | Old Cholmeleians v Old Amplefordians | Highgate School Ground, Highgate | 2010 |
| 26 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2021 |
| 25 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2003 |
| 25 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 2018 |
| 24 | Old Cholmeleians v Marlborough Blues | Highgate School Ground, Highgate | 2002 |
| 24 | Old Cholmeleians v Old Malvernians | Highgate School Ground, Highgate | 2004 |
| 22 | Old Cholmeleians v Old Alleynians | Dulwich College Ground, Dulwich | 1997 |
| 21 | Old Cholmeleians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 2000 |
| 21 | Old Cholmeleians v Old Wellingtonians | Highgate School Ground, Highgate | 2007 |
| 21 | Old Cholmeleians v Stowe Templars | Stowe School Ground, Stowe | 2013 |
| 21 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2023 |
| 20 | Old Cholmeleians v Felsted Robins | Highgate School Ground, Highgate | 1998 |
| 20 | Old Cholmeleians v Old Malvernians | Highgate School Ground, Highgate | 2006 |
| 19 | Old Cholmeleians v Repton Pilgrims | Repton School Ground, Repton | 1973 |
| 18 | Old Cholmeleians v Lancing Rovers | Lancing College Ground, Lancing | 1987 |
| 18 | Old Cholmeleians v Rugby Meteors | Highgate School Ground, Highgate | 1996 |
| 18 | Old Cholmeleians v St Edward's Martyrs | Highgate School Ground, Highgate | 1998 |
| 17 | Old Cholmeleians v Old Wellingtonians | Wellington College, Crowthorne | 2010 |
| 16 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 1969 |
| 16 | Old Cholmeleians v Old Cliftonians | Clifton College Close Ground, Clifton | 1985 |
| 16 | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | 1991 |
| 16 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 1996 |
| 16 | Old Cholmeleians v Marlborough Blues | Harman Drive, Brondesbury | 2017 |
