John Wakefield-54 (1615-1667), his wife, and children all lived and died in Boston. His widow Ann (1630-1703) remarried John Child in Boston after the death of Wakefield-54.
John Wakefield-102 (? -1660), his wife, and three daughters all lived and died in New Haven, Connecticut. His widow Ann (? -1695) remarried James Clark in New Haven after the death of Wakefield-102.
Despite the similar names they're completely different people.