Stockton-on-Tees, County Durham born inside left Billy Chesser had joined First Division club and FA Cup holders Bradford City from his hometown club Stockton in December 1911 but had to wait until February 1913 for his Football League debut which came at Oldham Athletic. He then scored on his home debut a week later in a 2-2 draw against Chelsea, but only made one further appearance in his breakthrough campaign. First team opportunities continued to prove limited and in February 1914 he signed for Second Division Lincoln City for a fee of £600 after a mere 2 goals in 7 matches for The Bantams.
At Lincoln he soon established himself as a first team regular missed only two matches in 1914-15 before the onset of the First World War forced the suspension of peacetime football in the summer of 1915. He played for Lincoln City regularly in the wartime competitions, and also made guest appearances for former club Bradford City. and after the War he returned to Sincil Bank for the 1919-20 season, indeed Chesser was Lincoln City’s leading scorer, though with only 8 goals, as the club finished in 21st place in the League and failed to gain re-election. He then stepped down another division to join newly elected Third Division club Merthyr Town in June 1920 having scored 20 goals in 78 appearances for The Imps (the Third Division being a new creation mainly formed from previous members of The Southern League).
He scored in Merthyr’s inaugural League match, a 2-1 victory over Crystal Palace (indeed it was Merthyr’s first ever League goal), but only stayed a single season in Wales before a move to Wigan Borough in September 1921, again for their first season in the Football League as founder members of the new Third Division (North) after 8 goals in 31 games for Merthyr. His season at Springfield Park produced a single goal in 13 matches, and he subsequently played for non league Lincoln Claytons in 1923 and had another brief spell on Lincoln City’s books in March 1924 without making their first eleven before his eventual retirement.