 By early in the 1925–26 season, Gilfillan was playing for Workington in the North Eastern League, scoring against Scotswood and twice against Hartlepools United reserves.In March 1926, he was a reserve for the Northern Counties team selected for a match against a Football Association eleven.The following season, he opened the scoring in Workington's first-round FA Cup match against Crook Town, but his team's overly casual attitude allowed the visitors to make a winning comeback.