His brother, John Hailwood (1870-1917), was killed in action while serving with the First AIF in Belgium on 4 October 1917.

[5][6] Hailwood played 150 games for Collingwood, including the 1902 Grand Final win over Essendon.

At the end of the 1899 season, in the process of naming his own "champion player", the football correspondent for The Argus ("Old Boy"), selected a team of the best players of the 1899 VFL competition: From those he considered to be the three best players — that is, Condon, Hickey, and Pleass — "Old Boy" selected Pat Hickey as his "champion player" of the season.

[7] On 22 April 1903 he was cleared from Collingwood to the Boulder City Football Club in the West Australian Goldfields Football Association (GFA).

[8] Although he was cleared from Collingwood Football Club to the Collingwood Juniors in July 1904,[9] he was reinstated in the senior team, playing in the last four of the last five home-and-away matches of the 1904 season, and in the 10 September 1904 Semi-Final team that lost to Fitzroy 7.8 (50) to 9.7 (61).