He made his debut in first-class cricket for Hampshire against Derbyshire at Southampton in 1885.
[1] Playing in the Hampshire side as a left-arm medium pace bowler, he took 25 wickets at an average of 22.56, with best figures of 4 for 39.
[3] With Hampshire losing their first-class status following that season, he continued to play minor matches for the county in 1886.
[4] Around the as he played first-class cricket for Hampshire, Willoughby founded the now defunct Botley F.C.
[7] He later stood as an umpire in the Minor Counties Championship in 1904 and 1905,[8] before standing in 21 first-class matches in 1906.