07 Jan2025 | Notts Co | Cheltenham | Free agent | |
| - | Solihull Moors | Notts Co | Return from loan | |
03 Mar2025 | Notts Co | Solihull Moors | Loan | |
| - | Barnsley | Notts Co | Free agent | |
07 Jan2022 | Bristol City | Barnsley | Free agent | |
| - | Gillingham | Bristol City | Return from loan | |
| - | Bristol City | Gillingham | Loan | |
| - | Cambridge Utd | Bristol City | Return from loan | |
08 Jul2020 | Bristol City | Cambridge Utd | Loan | |
| - | Torquay | Bristol City | Return from loan | |
09 Mar2019 | Bristol City | Torquay | Loan | |
07 Jan2019 | Bath | Bristol City | Transfer | |
09 Feb2019 | Exeter | Bath | Return from loan | |
07 Jan2019 | Bath | Exeter | Loan | |
| - | Gloucester | Bath | Transfer | |
08 Mar2017 | Oxford Utd | Gloucester | Free agent | |
| - | Southport | Oxford Utd | Return from loan | |
01 Sept2017 | Oxford Utd | Southport | Loan | |
01 Feb2017 | Oxford City | Oxford Utd | Return from loan | |
08 May2016 | Oxford Utd | Oxford City | Loan | |
| - | Gloucester | Oxford Utd | Return from loan | |
| - | Oxford Utd | Gloucester | Loan | |
| - | Chesham | Oxford Utd | Return from loan | |
| - | Oxford Utd | Chesham | Loan | |
| - | Daventry | Oxford Utd | Return from loan | |
| - | Oxford Utd | Daventry | Loan |
R. Cundy transfer history tracks all club moves during the professional career, including transfer dates and teams involved.