 In May 2008, Simmons was linked with Scottish First Division side Dundee and in July 2008 it was announced he was on trial with League Two side Morecambe.Simmons eventually signed a short-term deal with Scottish First Division side Queen of the South in September 2008.He played as a trialist for Raith Rovers in their Scottish Second Division league game against Peterhead in August 2008 and he made a second trialist appearance for Raith Rovers on Saturday 18 January 2009 at home to Stranraer.