A centre half back, Caulfield played nine senior VFL games late in the 1963 season.[2] He joined Port Melbourne in 1965 and would be the VFA club's captain until 1971. He made 118 appearances in total and won Port Melbourne's 'Best and Fairest' in his first season. At the 1966 Hobart Carnival, Caulfield represented the VFA.[3]
Western Australia 26.18 (174) defeated Victoria (VFA) 5.11 (41), at North Hobart Oval, 9 June 1966, crowd: 20,047 Tasmania 19.27 (141) defeated Victoria (VFA) 7.11 (53), at North Hobart Oval, 11 June 1966, crowd: 23,764 Victoria (VFL) 14.17 (101) defeated Victoria (VFA) 9.7 (61), at North Hobart Oval, 13 June 1966, crowd: 13,969 South Australia 21.20 (146) defeated Victoria (VFA) 9.11 (65), at North Hobart Oval, 16 June 1966, crowd: 10,199