| 9 | Haileybury Hermits v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2019 |
| 9 | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | 2021 |
| 8 | Haileybury Hermits v Old Merchant Taylors | Haileybury College Ground, Hertford | 1982 |
| 8 | Haileybury Hermits v Old Cheltonians | College Ground, Cheltenham | 2023 |
| 7 | Haileybury Hermits v Eton Ramblers | Haileybury College Ground, Hertford | 1976 |
| 7 | Haileybury Hermits v Old Whitgiftians | Haileybury College Ground, Hertford | 1984 |
| 7 | Haileybury Hermits v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 1993 |
| 7 | Haileybury Hermits v Old Tonbridgians | Haileybury College Ground, Hertford | 2024 |
| 6 | Haileybury Hermits v Old Westminsters | Haileybury College Ground, Hertford | 1969 |
| 6 | Haileybury Hermits v Old Malvernians | Malvern College Ground, Malvern | 1969 |
| 6 | Haileybury Hermits v Old Tonbridgians | Haileybury College Ground, Hertford | 1970 |
| 6 | Haileybury Hermits v Repton Pilgrims | Repton School Ground, Repton | 1971 |
| 6 | Haileybury Hermits v Charterhouse Friars | Haileybury College Ground, Hertford | 1983 |
| 6 | Haileybury Hermits v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2006 |
| 6 | Haileybury Hermits v Old Merchant Taylors | War Memorial Sports Ground, Merchant Taylors' School, Northwood | 2013 |
| 6 | Haileybury Hermits v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 2015 |
| 6 | Haileybury Hermits v Old Bedfordians | Haileybury College Ground, Hertford | 2025 |
| 5 | Haileybury Hermits v Rugby Meteors | Haileybury College Ground, Hertford | 1975 |
| 5 | Haileybury Hermits v Repton Pilgrims | Haileybury College Ground, Hertford | 1980 |
| 5 | Haileybury Hermits v Old Blundellians | Blundell's School, Tiverton | 1985 |
| 5 | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | 1992 |
| 5 | Haileybury Hermits v St Edward's Martyrs | Haileybury College Ground, Hertford | 1993 |
| 5 | Haileybury Hermits v Felsted Robins | Haileybury College Ground, Hertford | 1996 |
| 5 | Haileybury Hermits v Old Brightonians | Haileybury College Ground, Hertford | 2004 |
| 5 | Haileybury Hermits v Oundle Rovers | Oundle School Ground, Oundle | 2005 |
| 5 | Haileybury Hermits v Sherborne Pilgrims | Sherborne School, Sherborne | 2008 |
| 5 | Haileybury Hermits v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 2010 |
| 5 | Haileybury Hermits v Old Cranleighans | Haileybury College Ground, Hertford | 2018 |
| 4 | Haileybury Hermits v Old Alleynians | Haileybury College Ground, Hertford | 1970 |
| 4 | Haileybury Hermits v Repton Pilgrims | Haileybury College Ground, Hertford | 1970 |
| 4 | Haileybury Hermits v Repton Pilgrims | Burton's Court, Chelsea | 1983 |
| 4 | Haileybury Hermits v Old Merchant Taylors | Haileybury College Ground, Hertford | 1995 |
| 4 | Haileybury Hermits v Sherborne Pilgrims | Haileybury College Ground, Hertford | 1996 |
| 4 | Haileybury Hermits v Repton Pilgrims | Repton School Ground, Repton | 1997 |
| 4 | Haileybury Hermits v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1998 |
| 4 | Haileybury Hermits v Oundle Rovers | Haileybury College Ground, Hertford | 2000 |
| 4 | Haileybury Hermits v Old Brightonians | Brighton College Ground, Brighton | 2001 |
| 4 | Haileybury Hermits v Old Wykehamists | Ridding Field, Winchester | 2006 |
| 4 | Haileybury Hermits v Old Whitgiftians | Haileybury College Ground, Hertford | 2012 |
| 4 | Haileybury Hermits v Old Cranleighans | The Lowers, Cranleigh School | 2014 |
| 4 | Haileybury Hermits v Old Wellingtonians | Haileybury College Ground, Hertford | 2022 |
| 4 | Haileybury Hermits v Old Wellingtonians | Wellington College, Crowthorne | 2024 |
