Non-league football in the North of Scotland kicked off competitively in 1888. It did so with the introduction of a handsome solid silver trophy, namely the North of Scotland Junior Cup -- the "junior" tag inferring its status as a non-league association run outside of the confines of the "senior" Scottish Football Association. The first cup final was played at Cameron Barracks between the Crusaders and the Crown Strollers - two teams from Inverness, and result went the way of the former by a goal to nil. Following the cup final, a new association was formed to govern junior football in the North. Thus, a new tradition in the North of Scotland had been given life, and a prize now existed for all its teams to aspire to win. Such was the interest in the cup at this time, it attracted interest from several Inverness based senior teams (such as Clachnacuddin, Thistle and Caledonian) who each entered a "2nd XI" team.
The association introduced a league in 1896, principally to accommodate "2nd XI" teams from the Highland Football League (founded three years prior) which upon its formation mostly consisted of teams from Inverness and the surrounding area. Contrary to it's tag as a "2nd XI" league, it was won in its maiden year by Inverness Celtic, a first eleven side in their own right.
By the end of the First World War, the association had welcomed several new member teams from throughout Inverness-shire and Ross-shire such as Muir of Ord, Beauly, Dingwall Vics and Tore United. By 1948, the league was simply known as the North of Scotland "2nd XI" League or "North Reserve League", having dropped the "junior" tag altogether.
By the 1970s, the Highland Football League reserve teams which had frequently held membership gradually dropped out, with most finding that it was not a financially viable to run "2nd XI" or reserve team each season. At the same time, membership numbers rose as clubs from towns and villages throughout Ross and Sutherland joined the senior ranks, with as many as sixteen teams making up the league at one time.
In a bid to shake the stigma of the "reserve" tag, the remaining non-professional football clubs in the league took the decision to rename the league and at the 1984 annual general meeting of the North of Scotland 2nd XI Football Association in Bonar Bridge, member clubs voted unanimously to change the name of the association to the "North Caledonian Football Association" and the name of the league competition to the "North Caledonian Football League". By 1999, the league for the first time had no remaining "reserve" club members.
Throughout its existence, North Caledonian Football League has often characterised by the number of clubs who have used it as a 'stepping-stone' to the professional ranks of Scottish football. Perhaps the most historic was the emergence of Ross County who renamed themselves from Dingwall Victoria United, having left the league in 1929. Also among those to have 'graduated' from the North Caledonian League in more recent times are Fort William (in 1985) and Wick Academy (in 1994) who both left to join the Highland Football League.
In 2014, the league gained new significance as the first senior football association to accept memberships from the Scottish Islands, when Orkney Football Club were accepted into the league. As well as Orkney, Shetland FC and Lewis & Harris FC have also been accepted as frequent participants in some of the association's cup competitions. Today, the North Caledonian FA can proudly claim (with the exception of Argyle) to have representation from clubs belonging to every county in the Highlands and Islands.