| Extras |
| 63 | Uppingham Rovers v Old Cholmeleians | Highgate School Ground, Highgate | 2018 |
| 47 | Eton Ramblers v Old Cholmeleians | Highgate School Ground, Highgate | 2001 |
| 35 | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | 2003 |
| 35 | Old Merchant Taylors v Old Cholmeleians | Highgate School Ground, Highgate | 2009 |
| 34 | Old Whitgiftians v Old Cholmeleians | Whitgift School, Croydon | 2008 |
| 29 | Felsted Robins v Old Cholmeleians | Highgate School Ground, Highgate | 1998 |
| 29 | Old Malvernians v Old Cholmeleians | Highgate School Ground, Highgate | 2006 |
| 26 | Marlborough Blues v Old Cholmeleians | Harman Drive, Brondesbury | 2017 |
| 25 | Old Eastbournians v Old Cholmeleians | Eastbourne College Ground, Eastbourne | 2011 |
| 24 | Harrow Wanderers v Old Cholmeleians | Harrow School Cricket Ground, Harrow-on-the-Hill | 1992 |
| 24 | Old Wellingtonians v Old Cholmeleians | Highgate School Ground, Highgate | 2007 |
| 23 | Old Whitgiftians v Old Cholmeleians | Whitgift School, Croydon | 1979 |
| 23 | Rugby Meteors v Old Cholmeleians | Highgate School Ground, Highgate | 1985 |
| 23 | Old Alleynians v Old Cholmeleians | Dulwich College Ground, Dulwich | 1997 |
| 22 | Uppingham Rovers v Old Cholmeleians | Upper Field, Uppingham School | 1986 |
| 22 | Uppingham Rovers v Old Cholmeleians | Middle Field Pitch 1, Uppingham School | 2005 |
| 22 | St Edward's Martyrs v Old Cholmeleians | St Edward's School Ground, Oxford | 2023 |
| 21 | Old Wykehamists v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 21 | Sherborne Pilgrims v Old Cholmeleians | Sherborne School, Sherborne | 2015 |
| 19 | Stowe Templars v Old Cholmeleians | Stowe School Ground, Stowe | 1969 |
| 19 | Rugby Meteors v Old Cholmeleians | Rugby School Ground, Rugby | 1978 |
| 19 | Rugby Meteors v Old Cholmeleians | Highgate School Ground, Highgate | 1996 |
| 19 | Old Amplefordians v Old Cholmeleians | Highgate School Ground, Highgate | 2010 |
| 19 | Repton Pilgrims v Old Cholmeleians | Repton School Ground, Repton | 2025 |
| 18 | Downside Wanderers v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 18 | Old Amplefordians v Old Cholmeleians | Highgate School Ground, Highgate | 2007 |
| 17 | St Edward's Martyrs v Old Cholmeleians | St Edward's School Ground, Oxford | 2019 |
| 16 | Uppingham Rovers v Old Cholmeleians | Middle Field Pitch 1, Uppingham School | 2000 |
| 16 | Old Hurst Johnians v Old Cholmeleians | Hurstpierpoint College Ground, Hurstpierpoint | 2017 |
| 15 | Old Brightonians v Old Cholmeleians | Brighton College Ground, Brighton | 1993 |
