Becoming the starting Left Tackle during his rookie season, Holloways seemed to improve annually, and from 1983 to 1985, he was named to the Pro Bowl.  His best year was 1985, when he was a Second Team All-Pro, and helped the Patriots win the AFC Championship, though they would lose to the Chicago Bears. Holloway played one more year with the Pats before joining the Los Angeles Raiders for his final two seasons.

Throughout his Patriots career, Holloway only missed one game.