| 9 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 1969 |
| 8 | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | 1991 |
| 7 | Old Cholmeleians v Old Wykehamists | Highgate School Ground, Highgate | 1980 |
| 7 | Old Cholmeleians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1981 |
| 7 | Old Cholmeleians v St Edward's Martyrs | Highgate School Ground, Highgate | 1983 |
| 7 | Old Cholmeleians v Eton Ramblers | Upper Club, Eton College | 1990 |
| 7 | Old Cholmeleians v Old Blundellians | Blundell's School, Tiverton | 1994 |
| 7 | Old Cholmeleians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1997 |
| 7 | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | 1999 |
| 7 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2003 |
| 7 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2019 |
| 6 | Old Cholmeleians v Old Malvernians | Malvern College Ground, Malvern | 1975 |
| 6 | Old Cholmeleians v Charterhouse Friars | Highgate School Ground, Highgate | 1977 |
| 6 | Old Cholmeleians v Old Cliftonians | Clifton College Close Ground, Clifton | 1985 |
| 6 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 1996 |
| 6 | Old Cholmeleians v Old Malvernians | Highgate School Ground, Highgate | 2006 |
| 6 | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | 2009 |
| 6 | Old Cholmeleians v Old Cheltonians | College Ground, Cheltenham | 2014 |
| 6 | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | 2018 |
| 5 | Old Cholmeleians v Radley Rangers | Radley College Bigside Ground, Abingdon | 1970 |
| 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 Felsted Robins | Felsted School Ground, Dunmow | 1986 |
| 5 | Old Cholmeleians v Lancing Rovers | Lancing College Ground, Lancing | 1987 |
| 5 | Old Cholmeleians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1988 |
| 5 | Old Cholmeleians v Shrewsbury Saracens | Highgate School Ground, Highgate | 2002 |
| 5 | Old Cholmeleians v Old Wellingtonians | Wellington College, Crowthorne | 2010 |
| 5 | Old Cholmeleians v Marlborough Blues | Harman Drive, Brondesbury | 2017 |
| 5 | Old Cholmeleians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2023 |
| 5 | Old Cholmeleians v Old Brightonians | Brighton College Ground, Brighton | 2024 |
