While attending Stonehill, Chip played football all four years from 1984-1988 where he was a senior captain and an All-League Defensive End. At the time of his playing days, the Chieftains were a club team in the Northeast 10 Conference, but following his graduation, the College made the move to make football a varsity sport. The team during his senior captain season in 1988 was instrumental in moving Stonehill from club to varsity status and into Division III.
After graduation, he remained on the sidelines, but in a different role – as an assistant football coach in 1989 under Head Coach Cliff Sherman. That year the Chieftains competed in their first varsity season as a Division III team and won the ECFC Championship.