| 93 | Marlborough Blues v Old Cheltonians | Marlborough College Ground, Marlborough | 1976 |
| 107 | Old Cheltonians v Haileybury Hermits | College Ground, Cheltenham | 2011 |
| 167 | Old Cliftonians v Old Cheltonians | Clifton College Close Ground, Clifton | 2009 |
| 196 | Harrow Wanderers v Old Cheltonians | Harrow School Cricket Ground, Harrow-on-the-Hill | 1990 |
| 199 | Old Cheltonians v Radley Rangers | College Ground, Cheltenham | 1978 |
| 203 | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | 2002 |
| 233 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1972 |
| 239 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1986 |
| 240 | Bradfield Waifs v Old Cheltonians | Bradfield College, Reading | 1996 |
| 249 | Old Cheltonians v Repton Pilgrims | College Ground, Cheltenham | 1987 |
| 254 | Charterhouse Friars v Old Cheltonians | Charterhouse School, Godalming | 2024 |
| 257 | Old Cheltonians v Shrewsbury Saracens | College Ground, Cheltenham | 2006 |
| 265 | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | 1971 |
| 267 | Marlborough Blues v Old Cheltonians | Marlborough College Ground, Marlborough | 1970 |
| 272 | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | 1994 |
| 279 | Harrow Wanderers v Old Cheltonians | Harrow School Cricket Ground, Harrow-on-the-Hill | 1995 |
| 280 | Old Cheltonians v Oundle Rovers | College Ground, Cheltenham | 2019 |
| 284 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1974 |
| 291 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1985 |
| 291 | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | 2021 |
| 293 | Old Cheltonians v Old Amplefordians | College Ground, Cheltenham | 1974 |
| 293 | Old Cliftonians v Old Cheltonians | Clifton College Close Ground, Clifton | 1978 |
| 303 | Sherborne Pilgrims v Old Cheltonians | Sherborne School, Sherborne | 1983 |
| 331 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 1979 |
| 331 | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | 2014 |
| 339 | Old Cheltonians v Old Alleynians | College Ground, Cheltenham | 2013 |
| 340 | Downside Wanderers v Old Cheltonians | Downside School, Stratton-on-the-Fosse | 2021 |
| 342 | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | 2015 |
| 346 | Old Cheltonians v Old Tonbridgians | College Ground, Cheltenham | 1981 |
| 351 | Old Merchant Taylors v Old Cheltonians | Durrants Sports Ground, Croxley Green | 1998 |
