| 5 | Old Cholmeleians v Felsted Robins | Highgate School Ground, Highgate | 1971 |
| 5 | Old Cholmeleians v Old Whitgiftians | Whitgift School, Croydon | 1979 |
| 5 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1982 |
| 5 | Old Cholmeleians v Old Brightonians | Brighton College Ground, Brighton | 1993 |
| 5 | Old Cholmeleians v Shrewsbury Saracens | Highgate School Ground, Highgate | 2002 |
| 5 | Old Cholmeleians v Old Whitgiftians | Whitgift School, Croydon | 2008 |
| 5 | Old Cholmeleians v Stowe Templars | Stowe School Ground, Stowe | 2013 |
| 5 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2021 |
| 4 | Old Cholmeleians v Stowe Templars | Stowe School Ground, Stowe | 1969 |
| 4 | Old Cholmeleians v Radley Rangers | Radley College Bigside Ground, Abingdon | 1970 |
| 4 | Old Cholmeleians v Charterhouse Friars | Highgate School Ground, Highgate | 1977 |
| 4 | Old Cholmeleians v Rugby Meteors | Highgate School Ground, Highgate | 1985 |
| 4 | Old Cholmeleians v Uppingham Rovers | Upper Field, Uppingham School | 1986 |
| 4 | Old Cholmeleians v Lancing Rovers | Lancing College Ground, Lancing | 1987 |
| 4 | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | 1989 |
| 4 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1992 |
| 4 | Old Cholmeleians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 2000 |
| 4 | Old Cholmeleians v Old Malvernians | Highgate School Ground, Highgate | 2004 |
| 4 | Old Cholmeleians v Sherborne Pilgrims | Sherborne School, Sherborne | 2015 |
| 4 | Old Cholmeleians v Old Brightonians | Brighton College Ground, Brighton | 2024 |
| 3 | Old Cholmeleians v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1984 |
| 3 | Old Cholmeleians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1988 |
| 3 | Old Cholmeleians v Felsted Robins | Highgate School Ground, Highgate | 1998 |
| 3 | Old Cholmeleians v Eton Ramblers | Highgate School Ground, Highgate | 2001 |
| 3 | Old Cholmeleians v Marlborough Blues | Highgate School Ground, Highgate | 2002 |
| 3 | Old Cholmeleians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 2005 |
| 3 | Old Cholmeleians v Old Wellingtonians | Highgate School Ground, Highgate | 2007 |
| 3 | Old Cholmeleians v Radley Rangers | Radley College Bigside Ground, Abingdon | 2022 |
| 2 | Old Cholmeleians v Repton Pilgrims | Repton School Ground, Repton | 1976 |
| 2 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1981 |
| 2 | Old Cholmeleians v Stowe Templars | Stowe School Ground, Stowe | 1983 |
| 2 | Old Cholmeleians v St Edward's Martyrs | Highgate School Ground, Highgate | 1983 |
| 2 | Old Cholmeleians v Old Cliftonians | Clifton College Close Ground, Clifton | 1985 |
| 2 | Old Cholmeleians v Felsted Robins | Felsted School Ground, Dunmow | 1986 |
| 2 | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | 1991 |
| 2 | Old Cholmeleians v Old Blundellians | Blundell's School, Tiverton | 1994 |
| 2 | Old Cholmeleians v Old Alleynians | Dulwich College Ground, Dulwich | 1997 |
| 2 | Old Cholmeleians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1997 |
| 2 | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | 1999 |
| 2 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2003 |
| 2 | Old Cholmeleians v Old Malvernians | Highgate School Ground, Highgate | 2006 |
| 2 | Old Cholmeleians v Old Amplefordians | Highgate School Ground, Highgate | 2010 |
| 2 | Old Cholmeleians v Old Eastbournians | Eastbourne College Ground, Eastbourne | 2011 |
| 2 | Old Cholmeleians v Marlborough Blues | Marlborough College Ground, Marlborough | 2012 |
| 2 | Old Cholmeleians v Downside Wanderers | Tivoli Road, Hornsey | 2016 |
| 2 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 2018 |
| 2 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2023 |
| 2 | Old Cholmeleians v Repton Pilgrims | Repton School Ground, Repton | 2025 |
