[6][7][8] Dempsey led Moorefield to the 2014 Kildare Senior Football Championship, then returned to Westmeath as manager of the St Loman's club.
[4] His managerial record also ingludes leading the St Loman's club to the retention of a Westmeath Senior Football Championship title for the first time in its history, this achieved in 2016.
[11] He left after one season and was appointed manager of Longford GAA club Killoe Young Emmets in November 2022.
[4] However, he later moved to live in Westmeath after securing a job there in 1981, teaching mathematics at St Joseph's SC in Rochfortbridge.
[4] After setting out teaching there in 1981 as a 21-year-old, he managed St Joseph's Rochfortbridge to a Leinster Colleges Senior Football Championship title in 2020, a year before retiring.