Orr joined Liverpool in April 1908, when manager Tom Watson paid £350 for his transfer. He made his debut in a Football League Division One match at Villa Park against Aston Villa on 4 April 1908, bagging his first goal in the same match. Unfortunately for Orr and Liverpool, it was a consolation goal in a 5–1 defeat. This wasn't to be his only strike of the season, however, as he managed a more than respectable four goals in the final five matches of that season.