 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).Simmonds made his "Gills" debut in a 2–1 home win against Luton Town on 1 April.On 13 August 2008 Simmonds joined Kilmarnock on a loan deal set to last until 5 January 2009.