[11] He was the first-ever Collingwood player to represent Victoria, when he was selected to play against South Australia, at the MCG on 21 July 1894.

[12][13][14] The Collingwood vice-captain and real-life police constable Proudfoot was involved in an infamous incident during a game for Collingwood against North Melbourne on 25 July 1896 when a riot occurred at full-time, with the spectators invading the field, and North Melbourne supporters attacking both the umpire, former Carlton and VFA representative footballer Jack Roberts,[15] and a number of the Collingwood players:[16][17][18] While attempting to stop the umpire from getting injured, Proudfoot was badly beaten in the melee:[20] In the process of the official VFA investigation into the assault on Roberts (conducted on 6 April 1896) goal-umpire Wallace gave evidence that a 'North Melbourne barracker" had "threatened to put a knife into him".

[22] On 6 August 1896, one Samuel Fenton, "a powerfully-built man",[23] was charged with assaulting Proudfoot, was found guilty, and was sentenced to 3 months imprisonment.

[30][31] Following the formation of the Victorian Football League in 1897, Proudfoot played for Collingwood, against St. Kilda, at Victoria Park, on 8 May 1897, in the team's first-ever match of the VFL's first season.

[38] In speaking of Collingwood's best players on the day, Reginald Wilmot (i.e., "Old Boy" of The Age) noted that, "McKenna (who is said to be every bit as good a man as Proudfoot) ... did excellent work";[39][40] and a Collingwood-region newspaper noted the same relationship: In February 1903, Thomas O'Callaghan the Fifth Victorian Chief Commissioner of Police issued the following notification in the Victorian Police Gazette:[42] As a consequence of the commissioner's ban, he played in the 1903 Preliminary Final and Grand Final under the assumed name of "Bill Wilson".

[50] The Essendon team, under a police guard, was eventually able to escape the mob, via the tennis court on the Clifton Hill side of the ground, and reach their waiting transport.