| Extras |
| 49 | Old Cheltonians v Old Brightonians | Brighton College Ground, Brighton | 1999 |
| 48 | Old Cheltonians v Old Merchant Taylors | College Ground, Cheltenham | 2015 |
| 38 | Old Cheltonians v Eton Ramblers | Upper Club, Eton College | 2006 |
| 37 | Old Cheltonians v Marlborough Blues | College Ground, Cheltenham | 2023 |
| 35 | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | 2003 |
| 34 | Old Cheltonians v Old Wellingtonians | Wellington College, Crowthorne | 2015 |
| 32 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 2013 |
| 32 | Old Cheltonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2016 |
| 32 | Old Cheltonians v Marlborough Blues | Marlborough College Ground, Marlborough | 2017 |
| 29 | Old Cheltonians v Rugby Meteors | College Ground, Cheltenham | 2002 |
| 29 | Old Cheltonians v Sherborne Pilgrims | College Ground, Cheltenham | 2018 |
| 29 | Old Cheltonians v Old Merchant Taylors | Merchant Taylors' School Ground, Northwood | 2022 |
| 27 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 2007 |
| 27 | Old Cheltonians v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 2021 |
| 26 | Old Cheltonians v Haileybury Hermits | College Ground, Cheltenham | 2023 |
| 25 | Old Cheltonians v Haileybury Hermits | Haileybury College Ground, Hertford | 1992 |
| 25 | Old Cheltonians v Old Wellingtonians | College Ground, Cheltenham | 1995 |
| 25 | Old Cheltonians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 2022 |
| 24 | Old Cheltonians v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1998 |
| 24 | Old Cheltonians v Repton Pilgrims | Repton School Ground, Repton | 2012 |
| 23 | Old Cheltonians v Old Wellingtonians | Wellington College, Crowthorne | 2008 |
| 21 | Old Cheltonians v Old Amplefordians | College Ground, Cheltenham | 2001 |
| 21 | Old Cheltonians v Stowe Templars | Stowe School Ground, Stowe | 2015 |
| 20 | Old Cheltonians v Eton Ramblers | Upper Club, Eton College | 2005 |
| 20 | Old Cheltonians v Oundle Rovers | College Ground, Cheltenham | 2010 |
| 19 | Old Cheltonians v Charterhouse Friars | Charterhouse School, Godalming | 1984 |
| 19 | Old Cheltonians v Bradfield Waifs | Bradfield College, Reading | 1996 |
| 19 | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | 2014 |
| 18 | Old Cheltonians v Uppingham Rovers | College Ground, Cheltenham | 2011 |
| 18 | Old Cheltonians v Old Millfieldians | Millfield School, Street | 2025 |
