Born on 9 August 1883, "Titch" was the son of Millinda Sperring Stephenson and Alfred Shrapnell Bailes — who was the Mayor of Sandhurst,, and member of the Victorian Legislative Assembly — and he was also the older brother of one-time Collingwood footballer, Ernie Bailes. On one occasion, another younger brother, Alfred Bailes, a spectator at the match, took exception to a fierce charge made on "Titch" by Herbert Robinson, during the 27 July 1912 match between Brighton and Williamstown. Robinson had floored "Titch" and almost knocked him out. Alfred jumped the fence, chased Robinson and struck him. Alfred was later charged, by the police, with striking Robinson. He pleaded guilty to the charge. Bailes married Olive Amelia Lyons in 1911; they had three children, William, George, and Leonard.
Footballer
Perth
Recruited from the Bendigo Football Club, Bailes played the 1904 season with Perth as a rover.
Fitzroy
Initially used as a wingman, and later as a centre, Bailes transferred to Fitzroy from Perth in the 1905 — he had earlier played for a depleted Fitzroy team in an end-of-season charity match, in aid of the Bendigo Hospital, between Fitzroy and Collingwood in Bendigo in 1903, kicking one of Fitzroy's three goals in a drawn match. 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. Bailes won Fitzroy's Club Champion in 1907, and he represented Victoria at the Jubilee Australasian Football Carnival the following year, and "was brilliant on one of the wings" in Victoria's final match against Western Australia. He played in the first 15 matches of the 1909 season, and was then dropped for poor form. All in all he played 79 matches and scored 29 goals.
Brighton
His initial application for a transfer from Fitzroy to Brighton was refused at the VFL permit committee meeting on 27 April 1910: The matter was soon resolved; and he was granted a clearance on 4 May 1910. However, he did not play his first game for Brighton until the second round match, against Northcote, ten days later, on 14 May 1910, because the match in question, like all VFA and VFL matches originally scheduled for 7 May 1910, had been postponed for seven days as a mark of respect for King Edward VII, who had died at Buckingham Place on 6 May. In the last half of the 1913 season he was unable to play due to injury: Fully recovered, he played for Brighton in the first match of the 1914 season. He played in the centre with the Brighton, along with his brother Ernie, for six seasons.
Military Service
He enlisted in the First AIF in April 1916, served overseas, and was discharged in June 1919.
Coach
Sandringham
Bailes served as chairman of selectors for several years at the Sandringham Football Club in the VFA. In 1935, having retired from the Richmond Football Club at the end of the 1933 season, due to what had been considered to be a career-ending injury, and having worked as a football commentator for radio station3UZ for the entire 1934 VFL season, ex-Richmond wingman/half-forward Sid Dockendorff was appointed coach of Sandringham for the 1935 VFA season, in place of the former Essendon footballer, Garnet Campbell who had served as Captain-Coach in 1934. Dockendorff was cleared from Richmond to Sandringham in April 1935. He came out of retirement, and played at Sandringham as captain-coach. By late June, Dockendorff had obviously regained his pre-injury form; and was recruited by Syd Coventry, then the coach of Footscray, in a secret deal involving Richmond. At the end of June 1935, Dockendorff "asked for a clearance because of difficulties in effecting insurances against injury"; and, at a special meeting, the Sandringham officials granted his request. However, the very next day after the VFL had registered the clearance from Sandringham to Richmond, Richmond cleared Dockendorff to Footscray. 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. In these highly emotional circumstances, Bailes was appointed as coach of the Sandringham team for the remainder of the 1935 season; and, at the stage that Bailes took over the coaching, Brighton had only won three of the 12 matches it had already played that season — and it would go on to lose each of the final six matches of the 1935 season. There was further trouble when former Essendon footballer Clarrie Hearn was appointed captain-coach for the 1936 season. In June 1936, Hearn tendered his resignation, citing "pressure of business" — 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.
