| First Team Matches | Second Team Matches | Youth Team Matches | Associated with both clubs | Transfers | Ladies | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Cheltenham Manager | Referee | |
| 1974/75* | Friendly | 8 May 1975 | Horton Road, Gloucester | W | 7-2 | Billy McGarry | x | |
| 1987/88 | FA Cup | 14 November 1987 | Molineux | W | 5-1 | Graham Turner | John Murphy | C Downey (Hounslow) |
| 1999/00 | Friendly | 24 July 1999 | Whaddon Road | W | 1-0 | Colin Lee | Steve Cotterill | x |
| 2007/08 | Friendly | 28 July 2007 | Whaddon Road | W | 3-1 | Mick McCarthy | John Ward | x |
| 2014/15 | Friendly | 11 July 2014 | Whaddon Road | W | 3-1 | Kenny Jackett | Mark Yates | x |
* 1974/75 match was a combined Gloucester City & Cheltenham Town XI for a Testimonial match.
