 On 13 July 2008 the Kalamazoo Outrage qualified for the 2008 USL Premier Development League playoffs in their inaugural year.Riddle guided his side to second place in the Central Conferences Midwest Division narrowly finishing behind the Chicago Fire Premier in the regular season standings.His side would get their revenge eliminating the Chicago Fire Premier from the 2008 playoffs by virtue of a 2–0 victory at Toyota Park on 22 July.