 He was unable to maintain this level of form in the following years, however, and with the likes of Paul Hartley, Scott Severin and Phil Stamp preferred in central midfield, for the next 3 seasons he assumed the role of perpetual substitute, 41 of his 64 appearances coming from the bench.In January 2006, with Hearts, acquiring further competition for his favoured central midfield role allowed Simmons to leave Tynecastle, signing for Dunfermline on an initial 6-month deal.Due to an earlier cup appearance with Hearts, he was ineligible to appear in Dunfermline's League Cup campaign that season, in which they lost 3–0 to Celtic in the final.