[1] Junior football had been played in the region since the 1890s, but it was not until a restructuring across Scotland in the late 1960s that all teams in the territory were brought together under one umbrella - previously they had been competing in the local leagues in Angus,[2] Perthshire[3] and Dundee,[4] though the membership of these was not always rigidly dependent on geography, and another Midland League also existed from the 1920s to the 1940s involving clubs from all three territories.
With titles having been shared between clubs from Perthshire and Dundee (the sole Angus champions in 1974 being Kirrie Thistle), the league's balance altered dramatically in 1990 when Tayport joined the setup; their base was actually in the far north of Fife but they were permitted to join the Tayside league as they were closer to many of its teams via the Tay Road Bridge.
Despite the challenge of facing the strongest clubs from these other two areas, Tayport continued to be among the leading teams for the first six years; Dundee side Lochee United also finished as East Region champions twice in that period.
In 2018, a large group of East Junior clubs joined the East of Scotland Football League, aspiring to gain entry to the senior Scottish Professional Football League in future years;[6] however, on Tayside the only ones to do so were the Perth teams Jeanfield Swifts and Kinnoull.
This led to a North-South reorganisation of the remaining members of the region, with the 2019–20 Superleague North composed entirely of former Tayside clubs.