| 10 | Uppingham Rovers v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1997 |
| 8 | Uppingham Rovers v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1982 |
| 8 | Uppingham Rovers v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1989 |
| 8 | Uppingham Rovers v Bradfield Waifs | Upper Field, Uppingham School | 2014 |
| 7 | Uppingham Rovers v Repton Pilgrims | Upper Field, Uppingham School | 1970 |
| 7 | Uppingham Rovers v Old Westminsters | Vincent Square, Westminster | 1972 |
| 7 | Uppingham Rovers v Old Cholmeleians | Upper Field, Uppingham School | 1986 |
| 7 | Uppingham Rovers v Bradfield Waifs | Bank of England Ground, Roehampton | 1996 |
| 7 | Uppingham Rovers v Old Bedfordians | Bedford School Ground, Bedford | 2015 |
| 6 | Uppingham Rovers v Old Whitgiftians | Upper Field, Uppingham School | 1969 |
| 6 | Uppingham Rovers v Charterhouse Friars | Upper Field, Uppingham School | 1971 |
| 6 | Uppingham Rovers v Old Whitgiftians | Croham Manor Road, Croydon | 1972 |
| 6 | Uppingham Rovers v Old Tonbridgians | Burton's Court, Chelsea | 1979 |
| 6 | Uppingham Rovers v Old Brightonians | Brighton College Ground, Brighton | 1988 |
| 6 | Uppingham Rovers v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 2000 |
| 6 | Uppingham Rovers v Shrewsbury Saracens | Middle Field Pitch 1, Uppingham School | 2003 |
| 6 | Uppingham Rovers v Eton Ramblers | Middle Field Pitch 1, Uppingham School | 2004 |
| 6 | Uppingham Rovers v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 2012 |
| 6 | Uppingham Rovers v Old Merchant Taylors | Upper Field, Uppingham School | 2013 |
| 6 | Uppingham Rovers v Sherborne Pilgrims | Upper Field, Uppingham School | 2016 |
| 6 | Uppingham Rovers v Old Wykehamists | Upper Field, Uppingham School | 2016 |
| 6 | Uppingham Rovers v Old Bedfordians | Upper Field, Uppingham School | 2022 |
| 6 | Uppingham Rovers v Old Cranleighans | Jubilee, Cranleigh School | 2022 |
| 6 | Uppingham Rovers v Haileybury Hermits | Haileybury College Ground, Hertford | 2024 |
| 5 | Uppingham Rovers v Radley Rangers | Radley College Bigside Ground, Abingdon | 1967 |
| 5 | Uppingham Rovers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1968 |
| 5 | Uppingham Rovers v Old Amplefordians | Ampleforth College, Ampleforth | 1969 |
| 5 | Uppingham Rovers v Eton Ramblers | Upper Field, Uppingham School | 1973 |
| 5 | Uppingham Rovers v Old Wykehamists | Ridding Field, Winchester | 1974 |
| 5 | Uppingham Rovers v Old Wellingtonians | Wellington College, Crowthorne | 1976 |
| 5 | Uppingham Rovers v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1980 |
| 5 | Uppingham Rovers v Repton Pilgrims | Repton School Ground, Repton | 1982 |
| 5 | Uppingham Rovers v Lancing Rovers | Lancing College Ground, Lancing | 1983 |
| 5 | Uppingham Rovers v Felsted Robins | Felsted School Ground, Dunmow | 1985 |
| 5 | Uppingham Rovers v Old Malvernians | Malvern College Ground, Malvern | 1993 |
| 5 | Uppingham Rovers v Repton Pilgrims | Repton School Ground, Repton | 1995 |
| 5 | Uppingham Rovers v Bradfield Waifs | Bradfield College, Reading | 2002 |
| 5 | Uppingham Rovers v Marlborough Blues | Radley College Bigside Ground, Abingdon | 2006 |
| 5 | Uppingham Rovers v Felsted Robins | Middle Field Pitch 1, Uppingham School | 2007 |
| 5 | Uppingham Rovers v Repton Pilgrims | Middle Field Pitch 1, Uppingham School | 2009 |
| 5 | Uppingham Rovers v Old Cheltonians | College Ground, Cheltenham | 2011 |
| 5 | Uppingham Rovers v Old Malvernians | Upper Field, Uppingham School | 2018 |
