 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.On 28 March 2008, it was announced that Simmonds had joined Gillingham on loan until the end of the season, where he was given the number 2 (a number usually associated with right-backs).