| 5 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2014 |
| 4 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2021 |
| 4 | Old Cholmeleians v Repton Pilgrims | Repton School Ground, Repton | 2025 |
| 3 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 1969 |
| 3 | Old Cholmeleians v Felsted Robins | Highgate School Ground, Highgate | 1971 |
| 3 | Old Cholmeleians v Old Malvernians | Malvern College Ground, Malvern | 1975 |
| 3 | Old Cholmeleians v Old Wykehamists | Highgate School Ground, Highgate | 1980 |
| 3 | Old Cholmeleians v St Edward's Martyrs | Highgate School Ground, Highgate | 1983 |
| 3 | Old Cholmeleians v Old Cliftonians | Clifton College Close Ground, Clifton | 1985 |
| 3 | Old Cholmeleians v Old Alleynians | Dulwich College Ground, Dulwich | 1997 |
| 3 | Old Cholmeleians v Felsted Robins | Highgate School Ground, Highgate | 1998 |
| 3 | Old Cholmeleians v Shrewsbury Saracens | Highgate School Ground, Highgate | 2002 |
| 3 | Old Cholmeleians v Stowe Templars | Stowe School Ground, Stowe | 2013 |
| 3 | Old Cholmeleians v Marlborough Blues | Harman Drive, Brondesbury | 2017 |
| 3 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 2018 |
| 3 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2023 |
| 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 | 1982 |
| 2 | Old Cholmeleians v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1984 |
| 2 | Old Cholmeleians v Uppingham Rovers | Upper Field, Uppingham School | 1986 |
| 2 | Old Cholmeleians v Felsted Robins | Felsted School Ground, Dunmow | 1986 |
| 2 | Old Cholmeleians v Lancing Rovers | Lancing College Ground, Lancing | 1987 |
| 2 | Old Cholmeleians v Eton Ramblers | Upper Club, Eton College | 1990 |
| 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 Rugby Meteors | Highgate School Ground, Highgate | 1996 |
| 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 Eton Ramblers | Highgate School Ground, Highgate | 2001 |
| 2 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2003 |
| 2 | Old Cholmeleians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 2005 |
| 2 | Old Cholmeleians v Old Wellingtonians | Wellington College, Crowthorne | 2010 |
| 2 | Old Cholmeleians v Sherborne Pilgrims | Sherborne School, Sherborne | 2015 |
| 2 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2019 |
