[1][3] By January 1920, Dickson was part of a Darlington half-back line – the others being George Malcolm and Percy Sutcliffe – who, according to the Daily Express ahead of their FA Cup tie with Second Division Birmingham, had acquired "a reputation for upsetting opponents' designs".
[11] In September 1924, a crowd of 5,000 saw Scottish club Raith Rovers, with former Darlington player Peter Bell in their team, visit Feethams for Dickson's benefit match.
They struggled initially at the higher level; but by the turn of the year, Dickson and his fellow half-backs, Billy Robinson in the centre and Burridge on the left, were described as "sound",[13] and having "splendidly served" their teammates.
[14] For 1926–27, Darlington replaced Burridge with Jimmy McKinnell from Blackburn Rovers, and manager Jack English suggested the side would be "largely experimental", a blend of young players and more experienced men.
[15] At Fulham early in the season, Dickson reportedly found home forward Frank Penn "so clever that [he] seemed to give him up as a job too bad to be undertaken",[16] but later that month, he was the pick of Darlington's side and scored twice in a 4–2 defeat of Reading.
[17] He was injured in the fourth-round defeat to First Division Cardiff City in that season's FA Cup, initially moving out to the wing before having to leave the field entirely for half an hour.