| 6 | Uppingham Rovers v Haileybury Hermits | Middle Field Pitch 1, Uppingham School | 1979 |
| 6 | Uppingham Rovers v Rugby Meteors | Middle Field Pitch 1, Uppingham School | 1981 |
| 6 | Uppingham Rovers v Sherborne Pilgrims | Middle Field Pitch 1, Uppingham School | 1987 |
| 6 | Uppingham Rovers v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1987 |
| 6 | Uppingham Rovers v Charterhouse Friars | Upper Field, Uppingham School | 2017 |
| 5 | Uppingham Rovers v Oundle Rovers | Oundle School Ground, Oundle | 1977 |
| 5 | Uppingham Rovers v Radley Rangers | Radley College Bigside Ground, Abingdon | 1992 |
| 5 | Uppingham Rovers v Charterhouse Friars | Middle Field Pitch 1, Uppingham School | 1998 |
| 5 | Uppingham Rovers v Old Amplefordians | Middle Field Pitch 1, Uppingham School | 2002 |
| 5 | Uppingham Rovers v Shrewsbury Saracens | Upper Field, Uppingham School | 2018 |
| 5 | Uppingham Rovers v Haileybury Hermits | Haileybury College Ground, Hertford | 2021 |
| 4 | Uppingham Rovers v Old Wellingtonians | Upper Field, Uppingham School | 1971 |
| 4 | Uppingham Rovers v Old Whitgiftians | Croham Manor Road, Croydon | 1972 |
| 4 | Uppingham Rovers v Old Wykehamists | Ridding Field, Winchester | 1974 |
| 4 | Uppingham Rovers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1975 |
| 4 | Uppingham Rovers v Lancing Rovers | Lancing College Ground, Lancing | 1983 |
| 4 | Uppingham Rovers v Shrewsbury Saracens | Middle Field Pitch 1, Uppingham School | 1984 |
| 4 | Uppingham Rovers v Old Tonbridgians | Middle Field Pitch 1, Uppingham School | 1984 |
| 4 | Uppingham Rovers v Rugby Meteors | Middle Field Pitch 1, Uppingham School | 1990 |
| 4 | Uppingham Rovers v Eton Ramblers | Agar's Plough, Eton College | 1992 |
| 4 | Uppingham Rovers v Old Malvernians | Malvern College Ground, Malvern | 1993 |
| 4 | Uppingham Rovers v St Edward's Martyrs | St Edward's School Ground, Oxford | 2002 |
| 4 | Uppingham Rovers v Bradfield Waifs | Bradfield College, Reading | 2002 |
| 4 | Uppingham Rovers v Old Tonbridgians | Middle Field Pitch 1, Uppingham School | 2010 |
| 4 | Uppingham Rovers v Old Cheltonians | College Ground, Cheltenham | 2011 |
| 4 | Uppingham Rovers v Sherborne Pilgrims | Upper Field, Uppingham School | 2016 |
| 4 | Uppingham Rovers v Old Brightonians | Spen Cama Memorial Ground, Fulking | 2019 |
| 4 | Uppingham Rovers v Old Cliftonians | Upper Field, Uppingham School | 2023 |
| 3 | Uppingham Rovers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1968 |
| 3 | Uppingham Rovers v Charterhouse Friars | Upper Field, Uppingham School | 1971 |
| 3 | Uppingham Rovers v Eton Ramblers | Upper Field, Uppingham School | 1973 |
| 3 | Uppingham Rovers v Old Wellingtonians | Wellington College, Crowthorne | 1976 |
| 3 | Uppingham Rovers v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1978 |
| 3 | Uppingham Rovers v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1980 |
| 3 | Uppingham Rovers v Old Cholmeleians | Upper Field, Uppingham School | 1986 |
| 3 | Uppingham Rovers v Old Wellingtonians | Middle Field Pitch 1, Uppingham School | 1987 |
| 3 | Uppingham Rovers v Old Brightonians | Brighton College Ground, Brighton | 1988 |
| 3 | Uppingham Rovers v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1993 |
| 3 | Uppingham Rovers v Bradfield Waifs | Middle Field Pitch 1, Uppingham School | 1994 |
| 3 | Uppingham Rovers v Repton Pilgrims | Repton School Ground, Repton | 1995 |
| 3 | Uppingham Rovers v Old Amplefordians | Middle Field Pitch 1, Uppingham School | 1999 |
| 3 | Uppingham Rovers v Shrewsbury Saracens | Middle Field Pitch 1, Uppingham School | 2003 |
| 3 | Uppingham Rovers v Eton Ramblers | Middle Field Pitch 1, Uppingham School | 2004 |
| 3 | Uppingham Rovers v Old Merchant Taylors | Upper Field, Uppingham School | 2013 |
| 3 | Uppingham Rovers v Old Bedfordians | Bedford School Ground, Bedford | 2015 |
| 3 | Uppingham Rovers v Old Wykehamists | Upper Field, Uppingham School | 2016 |
