Sampson started his league career in 1907 with Port Adelaide and by the time he retired in 1921 he had played 161 games (he later added two more as coach) and was a dual Magarey Medalist. He won his first award in 1910 and in 1915 was involved in a three way tie but ultimately lost in a count back to Frank Barry. In 1998 however the league awarded those who had lost in this fashion retrospective Medals and thus joined club greats Bob Quinn and Russell Ebert as the only Port Adelaide players to win the award twice. During his playing career Sampson also represented South Australia at interstate football, appearing 10 times in total.
Hosking was self-confessed as "one of the dirtiest players who ever stripped" and many find it amazing that he won two Magarey Medals as the award is presented to the SANFL's best and fairest player. But Hosking was far from a self-confessed thug. He was a fast, fierce, accurate and determined player who never gave an inch in an era when dirty play was often overlooked by officials. In the early days of the SANFL and Australian rules football in general, only one umpire officiated a game so behind play clashes, for which Hosking and others were notorious, more often than not went unseen.
After retiring from playing, Hosking turned his vast football experience to coaching. He coached West Adelaide to the 1922 SANFL Grand Final where The Bloods lost to Norwood 9.7 (61) to 2.16 (28) in front of 31,000 at the Adelaide Oval. In 1927 he became coach of Port Adelaide and guided the club to three premierships. He also coached West Torrens to a premiership in 1933 and the short lived merged Port Adelaide-West Torrens Football Club to a premiership during World War II.
Despite having retired from playing after 1921, in 1936 he became the oldest SANFL player when at the age of 48 he sat on the bench for one game for Port Adelaide. The record of the oldest player still stands as of December 2013 and is a record that is unlikely to be broken.