From his debut in the fifth round of the 1959 VFL season until midway through the 1964 season, Grimmond did not miss a single game for Richmond.
Grimmond usually played as a wingman and after being appointed captain-coach of North Hobart in 1965, promptly steered the club to a Grand Final loss. He represented Tasmania in the 1966 Hobart Carnival.
Victoria (VFL) 26.24 (180) defeated Tasmania 11.13 (104), 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 Western Australia 17.13 (115) defeated Tasmania 16.10 (106), at North Hobart Oval, 16 June 1966, crowd: 10,199 South Australia 14.7 (91) defeated Tasmania 9.13 (67), at North Hobart Oval, 18 June 1966, crowd: 23,368