[3] Born in Barrhead,[4] Logan began his senior career with local club Arthurlie of Scotland's second tier in 1908, moving to Falkirk, at that time one of the top teams in the country, in 1910, following a trial.
[5][6] During the initial months of his first season at Brockville Park (in which the club eventually finished in third place), his elder brother Alec[4] was a teammate prior to a transfer to England; another older sibling James[4] was also a professional footballer who played in England, becoming an opponent after he moved back home in 1912 to play with Rangers.
[7] With the Bairns, Logan lifted the Scottish Cup after a 2–0 win over Raith Rovers in the 1913 final at Celtic Park, scoring the second goal;[8][9][10] it was the club's first major honour, and he joined Chelsea within a few weeks.
He was one of the few Chelsea players to get a positive mention in the Manchester Guardian report on the final for a few "dashing excursions" into the Sheffield half, he failed to score.
[13] By then, he was judged to be "an ideal centre half who showed judgement in his play",[11] although in his early years he had been considered a forward and had a good scoring ratio for Falkirk.