He played hurling with his local club Buffer's Alley and with the Wexford senior inter-county team from 1984 until 2000.
1988 saw Dempsey won another county title before later adding a second Leinster club medal to his collection.
Once again Buffer's Alley reached the All-Ireland final, this time with O’Donovan Rossa of Antrim providing the opposition.
[2] In 1993 Dempsey was captain as Wexford looked set for glory when they reached the final of the National Hurling League.
In the final of that competition Wexford drew with arch rivals and All-Ireland champions Kilkenny and there was hope of success.
Wexford later defeated Galway in the penultimate game of the championship, setting up an All-Ireland final meeting with Limerick.
Dempsey was the hero of the day as he scored a goal after nineteen minutes to give Wexford a major advantage.
[3] Dempsey captured a second Leinster medal in 1997 as Kilkenny fell in the provincial decider.
1997 saw the introduction of the so-called ‘back-door’ system whereby the defeated Munster and Leinster finalists were allowed back into the All-Ireland championship at the quarter-final stage.
He won his sole Railway Cup medal in 1993 as Leinster defeated Ulster.