O'Brien started his career playing junior football in the Glasgow, playing for Elm Park and Glasgow Northern,[1] before making the move south to join London side Woolwich Arsenal in 1894.
[2] An injury at the start of the 1895–96 season ruled O'Brien out for four months, hampering his goal tally.
[2] However, despite this, he was sold to Bristol City in the summer of 1897, linking up with former Arsenal boss Sam Hollis, who had also just moved there.
[3] He spent five years with Bristol City before seeing out his career with Swindon Town,[4] making a single appearance for the Robins in 1902–03.
This biographical article related to association football in Scotland, about a forward born in the 1870s, is a stub.