 Simpson went to Stanborough School in Welwyn Garden City until he was 16.Whilst playing for Cambridge City, Simpson obtained good A-levels, and decided to follow this by studying for a degree in Sports Science and Mathematics at Loughborough University (graduating in 2007) whilst remaining tied to the club though coaching in their 'Youth in the Community' scheme.Robbie won the British Universities Sport Association trophy all three years when he was there playing for the student team, now Loughborough University F.C..

Simpson made his first team debut for Cambridge City in October 2002.