After injury ended his career in 1966, he turned his hand to coaching, at Portsmouth and then, with greater success, at Queens Park Rangers. He went on to work under Bertie Mee at Arsenal as first-team coach, after Steve Burtenshaw's resignation and subsequent departure to Sheffield Wednesday in 1973.

His first managerial job came at Fulham in 1976, after his former boss Alec Stock was sacked. He made a poor start winning no games in his first 3 months as manager. After four years of underachievement Bobby was sacked when the team made a poor start to the 1980–81 season after a disastrous relegation the previous season.

He moved on to Portsmouth, whom he led to the Third Division title in 1982–83. However, he was sacked in May 1984 after Portsmouth only narrowly avoided being immediately relegated back to the Third Division. Bobby then returned to Queens Park Rangers for a stint as reserve team manager, before taking up the same position at Chelsea in the summer of 1987.

Towards the end of the 1987–88 season, he was appointed assistant to manager John Hollins, with the team in the midst of a relegation battle; one month later Hollins was sacked and Bobby appointed caretaker manager until the end of the season. He was unable to turn around the club's fortunes in the eight games which remained that season, and they were relegated via the short-lived play-off system.

He made amends the following season, however, as his side romped to promotion as Second Division champions with a haul of 99 points. A year later, he led to Chelsea to a 5th-place finish in the First Division, their highest league placing since 1970. He was relieved of his managerial duties after an 11th-place finish and appointed personal assistant to Chelsea chairman Ken Bates in 1991.

Bobby went on to coach in Kuwait where he managed the two biggest clubs in the country: Al-Arabi SC and Qadsia SC.

After injury ended his career in 1966, he turned his hand to coaching, at Portsmouth and then, with greater success, at Queens Park Rangers. He went on to work under Bertie Mee at Arsenal as first-team coach, after Steve Burtenshaw's resignation and subsequent departure to Sheffield Wednesday in 1973.

His first managerial job came at Fulham in 1976, after his former boss Alec Stock was sacked. He made a poor start winning no games in his first 3 months as manager. After four years of underachievement Bobby was sacked when the team made a poor start to the 1980–81 season after a disastrous relegation the previous season.

He moved on to Portsmouth, whom he led to the Third Division title in 1982–83. However, he was sacked in May 1984 after Portsmouth only narrowly avoided being immediately relegated back to the Third Division. Bobby then returned to Queens Park Rangers for a stint as reserve team manager, before taking up the same position at Chelsea in the summer of 1987.

Towards the end of the 1987–88 season, he was appointed assistant to manager John Hollins, with the team in the midst of a relegation battle; one month later Hollins was sacked and Bobby appointed caretaker manager until the end of the season. He was unable to turn around the club's fortunes in the eight games which remained that season, and they were relegated via the short-lived play-off system.

He made amends the following season, however, as his side romped to promotion as Second Division champions with a haul of 99 points. A year later, he led to Chelsea to a 5th-place finish in the First Division, their highest league placing since 1970. He was relieved of his managerial duties after an 11th-place finish and appointed personal assistant to Chelsea chairman Ken Bates in 1991.

Bobby went on to coach in Kuwait where he managed the two biggest clubs in the country: Al-Arabi SC and Qadsia SC.