Cuppett played football for four years under Coach Underwood and graduated in 1962. While at Salem, he was married with two children, worked part-time during the school year and full time during the summers in the mines. He was selected to WVIAC All Conference football teams for three years. The pinnacle of recognition for his time at Salem was his selection for the All time WVIAC Football Team (1924-1974) at the 1974 induction.
After Graduating with a bachelor's degree in education, Cuppett went on to teach social studies and physical education at the junior and senior high levels, where he also coached basketball, football, and golf. He was an athletic director for 16 years . His overall record for coaching three sports in tow states over thirty years is 404-151-2 and his teams won or were runners-up for 45 sectional, district, regional and/or state championships. Eight of his teams received Top Ten rankings.
Over his career, he has been honored with numerous awards, including the Education Emeritus Award by the Chillicothe Education association, the Ohio Capitol Conference Athletic Administrator's Hall of fame, the Chillicothe High School Athletic Hall of Fame and the Ohio High School Basketball Coaches's Hall of Fame, he was also honored by the Mayor of Chillicothe in 1993 with a day named in his honor. He has also won "Man of the Year" and "Teacher of the Year" awards.