|Bobby started out in his native Devon as a youth player with Plymouth Argyle, joining the side in July 2006. Although he featured in the Pilgrimsí side that reached the quarter finals of the FA Youth Cup in 2007/08, he left without appearing for the first team in April 2008 and joined Southern League Premier Tiverton Town ahead of interest from AFC Bournemouth.
Having impressed enough to win two Player of the Season awards through the 2008/09 season, he left Tiverton for Aldershot Town on non-contract terms in August 2009.
However, during his time with the League Two side he appeared just twice in competitive games, while also playing for Farnborough Town on a dual registration in January 2010 - where he made four appearances and scored one goal. He was released by Aldershot in March 2010 and joined the Hawks a fortnight later.
He quickly became a regular starter in the side and a fan favourite until a spiral crack in his tibia sustained during a game against Boreham Wood in January 2011 kept him off the pitch for the rest of the season.
Returning to the game in November of that year, he made his presence felt mostly through substitute appearances last season, bringing his overall tally to 47.
Having struggled to regain his original form after his lengthy injury, Bobby was released in August 2012.