Following the end of a loan to Oxford City during the first half of the 2016–17 season, Cundy was loaned to Southport for a month.[7] He was released by Oxford United at the end of the season. After spending pre-season with Kidderminster Harriers, Cundy re-signed for National South side Gloucester City.[8]
Cundy won the National League North's player of the month award in February 2016. He attended Fitzharrys Secondary School.
After the conclusion of the 2018–19 season, in which he made 48 appearances in all competitions for Bath City, and won the clubs' Supporters' Player of the Year, Players' Player of the Year, and Manager's Player of the Year Awards, Cundy signed for Championship side Bristol City on a two-year contract, with an option of another additional year.[10]
Following his arrival at Bristol City, Jerry Gill, manager of Bath City, said [about Robbie Cundy]: 'He was by far one of the best centre-backs in the league and he deservedly won all the awards at our end of season dinner."[11]
On 25 January 2021, Cundy joined League One side Gillingham on loan for the remainder of the 2020-21 season.[12]
Cundy joined Barnsley for the start of the 2022–23 season. On 17 May 2024, the club announced he would be released in the summer when his contract expired.[13]
Career statistics
As of match played 12 March 2022
Appearances and goals by club, season and competition