Massimino coached for 30 years at the NCAA level. He began his coaching career at Stony Brook where he compiled a 34-16 record in two years. His next stop was at Villanova, where he spent 19 years as the Wildcats' coach and amassed 357 wins. Massimino's 1984-85 Villanova team defeated conference rival Georgetown in the NCAA championship game in one of the greatest upsets in tournament history. In addition to the national title, Massimino's teams won five conference championships and received 12 NCAA tournament bids. He went on to coach at UNLV and Cleveland State for nine years. He currently coaches Northwood University in West Palm Beach, Florida.