Sheppard first played Gaelic football and hurling at juvenile and underage levels with the Kilruane MacDonaghs.[1] After winning numerous divisional titles in the minor and under-21 grades, he progressed onto the club's respective senior teams and won a combined total of 12 North Tipperary titles across both codes between 1976 and 1990. He captained Kilruane MacDonaghs to the All-Ireland Club Championship title in 1986, having earlier won four Tipperary SHC titles.[2][3]