Born on 9 August 1883,[8] "Titch" was the son of Millinda Sperring Stephenson (1851-1902)[9] and Alfred Shrapnell Bailes (1849-1928) — who was the Mayor of Sandhurst, (1883-1884), and member of the Victorian Legislative Assembly (1896-1894, 1897–1907)[10][11] — and he was also the older brother of one-time Collingwood footballer, Ernie Bailes.

[25] He finished 1905 in a premiership side; Fitzroy defeated Collingwood in a low scoring Grand Final, and was regarded as the best player on the ground.

His initial application for a transfer from Fitzroy to Brighton was refused at the VFL permit committee meeting on 27 April 1910:[32] The matter was soon resolved; and he was granted a clearance on 4 May 1910.

At the end of June 1935,[47] Dockendorff "asked for a clearance [back to Richmond] because of difficulties in effecting insurances against injury"; and, at a special meeting, the Sandringham officials granted his request.

[49] He eventually played 17 senior games for Footscray; and Coventry eventually came good on his promise to Dockendorff, and Dockendorff was promoted to the position of club captain (he was captain in 1937, although only playing in 4 matches, and retiring due to injury).

In June 1936, Hearn tendered his resignation, citing "pressure of business"[52] — however, on this occasion, rather than, once again, calling on Bailes, the club decided to split the coaching duties between the captain, Bob Thoms, as captain-coach, and the vice-captain, Bill Mitchell, as his assistant, for the rest of the season.