 Simmonds joined Coventry City on a free transfer, signing a two-year deal following his release from the Charlton Athletic academy at the end of the 2006–07 season.Simmonds had impressed while on trial, playing in two friendly matches and a testimonial match against Nuneaton Borough, in which he netted in a 5–0 win.He was one of a number of Coventry signings to have previously worked with manager Iain Dowie during their brief time together at Charlton.