Simpson first came to note as a rugby player when he was chosen to represent Cambridge University; and earned a single sporting 'Blue' as part of the Cambridge team in The Varsity Match of 1890. The same year he completed his university education, Simpson was invited, along with several other Cambridge players, to join Bill Maclagan's British Isles team on a tour of South Africa. Simpson played ten matches over the tour, but was only selected for one Test match.[3] Simpson's one and only international cap was the First Test against South Africa, which was played at Port Elizabeth, the tourists winning 4–0.
On his return from South Africa, Simpson joined Richmond Rugby Club, and in 1893 was selected to play for invitational touring team, the Barbarians.[4]