Right-half Bobby was captain of the West Kensington Central School football team and won representative honours with Middlesex Schools and London Schools, and took part in an England schoolboy international trial. Leaving school at 14 he joined Chelsea and played for their junior and youth teams before joining Wimbledon in 1955.

He established himself as the first choice right-half during the 1956/57 season, although when required he could play anywhere across the half-back line.

Bobby was a cornerstone of the successful Wimbledon side of the 1960s and appeared in the 1963 FA Amateur Cup final. He played 12 times for the England Amateur team, leading them out as captain on four occasions and scoring on his debut against Wales. He also played for Great Britain against Iceland in a qualifying match for the 1964 Olympics.

Courted early in his career by the likes of West Bromwich Albion, Aston Villa, Fulham and Charlton Athletic, Bobby turned them all down and remained with Wimbledon until 1971.

And electrical engineer, Bobby was fond of modern jazz and part of the Club's golf team.