Cantafio spent a total of eleven seasons as a head coach, with the Virginia Military Institute (1986–1994) and Furman University (1994–1997).
[3] Cantafio began coaching immediately following his graduation from Scranton, joining Cardinal Gibbons High School in Raleigh, North Carolina, in 1974.
Following a 13–15 campaign at Abington Heights, Cantafio then joined DeMatha Catholic High School as an assistant where he served under legendary Morgan Wootten (who has the second most wins as a head coach in the history of basketball on any level and is a member of the Naismith Basketball Hall of Fame).
In 1982, Cantafio left for an assistant coaching job at the Virginia Military Institute where he worked under his predecessor Marty Fletcher for four seasons.
[5][page needed] Cantafio resigned following the 1993–94 season and became the head coach of the Furman Paladins, a Southern Conference foe of VMI.
"[8] Cantafio also stated that he was unable to relax while coaching, and that some Furman boosters and alumni were not happy with the team's progress.