Ryan has progressed through the Millers youth system and last season the young striker became a first team regular. He made his senior debut as a substitute in December 2005 in a 1-0 defeat by Swindon but did not feature again till August 2006. During the 2006/07 season Ryan made 10 first team appearances, mostly from the bench and spent the start of last season on loan at Burton Albion. His time at Burton was short as he was recalled to play a major role in the Millers rise up the table. Ryan scored his first senior goal for Rotherham in a 2-0 victory over Shrewsbury and finished the 2007/08 campaign with six goals.