Although outside-right Speakman was at Anfield for four seasons just before World War I, he only played eight times for the first team. Arthur Goddard was Liverpool's right-winger during the 1909/10 season and missed only three first division matches that year, being replaced by Speakman for two of them. Speakman fared little better the following season, being restricted to just a single appearance - again as cover for Goddard. James was the younger brother of Sam, who was also on Liverpool's books. James' attributes were so described in the club programme on 25 October 1909: "Speakman stands 5ft. 8 in. and weighs 11 st. 10 lbs. He possesses a useful turn of speed, and is much faster than would seem to be the case for when running he moves with little apparent effort. In controlling the ball and passing it across the goal mouth he greatly resembles Goddard whose understudy he is, and the similarity of style of the two right wingers is quite convincing."

During 1911/12, numerous changes were made to Liverpool's line-up in a turbulent season which saw them finish just outside the relegation zone. Speakman figured in three consecutive games towards the end of that season, during which he netted his only Liverpool goal at Bradford City. He would only play once more for the club, almost a year later, as part of the team that lost at home to Manchester United on 29 March 1913.