Beith, Ayrshire born centre forward Jackie Chalmers started his football career with Rutherglen Glencairn in 1903 before turning professional with Glasgow Rangers in 1904. He made his debut for Rangers in a Scottish Cup first round tie against Ayr Parkhouse in January 1905, scoring in a 2-1 victory at Ibrox. He then scored in his second match for Rangers, a 5-1 Scottish Cup third round victory over Beith almost a month later, but only made his Scottish League debut, and sole appearance for The Gers, at the end of April in a 2-0 win at Morton.
Unable to break into the Rangers team, he moved to First Division Stoke City in January 1906 and again made an instant impact scoring on his Football League debut in a 2-2 draw with Derby County in March 1906 and notching five goals in his first five games. He was the club’s top scorer in the 1906-07 season with 11 goals, though they were relegated from the First Division at the season end. In all he scored 19 goals in 43 appearances but was released in the summer of 1907. He had a spell at Southern League Bristol Rovers, before moving back north of the border to join Clyde in November 1908. In 1909–10 Chalmers was in Clyde’s side that reached the Scottish Cup Final, which they eventually lost to Dundee in the second replay.
In October 1910 Chalmers was tempted south of the border again, signing for Woolwich Arsenal. Arsenal had been ailing in the First Division; they had only scored twice in their first six matches of the 1910-11 season and were languishing in seventeenth place. Chalmers made his debut against Bradford City on October 8th 1910 and had an immediate impact on Arsenal’s season, scoring fifteen league goals (and one in the FA Cup, making him the club’s top scorer) as Arsenal finished a comfortable tenth. Chalmers was a first-team starter the next season, but lost his place to Alf Common, who had been moved from inside forward to centre forward. Chalmers was unhappy playing for Arsenal’s reserves and was transferred to Morton in March 1912. He played for West Stanley and before re-joining Clyde later in 1913 and joined Irish League Shelbourne in 1914 before retiring from playing, later becoming a trainer at Clyde.