Whitcroft played for several notable amateur and early professional hockey squads, including the Renfrew Creamery Kings, Edmonton Eskimos and Kenora Thistles, between 1906 and 1910.

[citation needed] The following year Whitcroft signed a contract to play with the Edmonton Eskimos of the Alberta Professional Hockey League.

Edmonton played in one Stanley Cup challenge in 1908, coming up against the Wanderers, losing 13-10 on goals in a two-game series.

After the Edmonton team disbanded in December 1909, Whitcroft jumped back east and signed with the National Hockey Association's Renfrew Creamery Kings for $2,000.

[citation needed] He took up gold prospecting after his hockey career was over, while also coaching the Edmonton team for the Patricks, his former teammates.