Simmons made his club debut on 11 May 2008, the final day of the season, in a Premier League game, for Derby County against Reading as a substitute.
[3] Simmons first team chances were restricted by Paul Jewell's squad reconstruction following relegation from the Premier League and, on 30 October 2008, he joined non-league Burton Albion on a month's loan.
[5] After joining Wolverhampton Wanderers on trial[citation needed] he signed for Conference North team Eastwood Town.
Simmons moved to the United States in 2011 when he signed with the New Orleans Jesters in the USL Premier Development League.
He made his debut for the Jesters in their first game of the 2011 season, a 3–1 loss to the El Paso Patriots,[7] and scored his first goal on 21 May, in a 2–0 win over the West Texas United Sockers.