Scotland Highland League

The Highland Football League was formed on 4 August 1893, at the Inverness Workman's Club by employees of the Highland Railway Company who had their Company Headquarters, Locomotive and Carriage & Wagon Workshops (Loch Gorm Works), based in the Highland capital and where they employed circa 700 staff. The original league consisted of seven teams: Inverness Thistle, Caledonian, Clachnacuddin, Forres Mechanics, Inverness Union, Inverness Citadel and Cameron Highlanders. Dingwall Victoria United (later renamed Ross County) were an eighth original member, but resigned membership in November 1893. The inaugural champions were Inverness Thistle. Of the original teams, two are still playing in the league today (Clachnacuddin and Forres Mechanics) while Caledonian and Thistle merged to become current Scottish League club Inverness Caledonian Thistle.

The league has been somewhat weakened by the departure of many former members who have subsequently joined the SFL. In 1994, Caledonian, Inverness Thistle and Ross County left. Until then the HFL had operated with 18 clubs; this was reduced by the departure of the three mentioned clubs, but Wick Academy from the North Caledonian Football League were elected, to create a league of 16 clubs. This was the state of affairs till 2000 when Elgin City and Peterhead were elected into the SFL. In 2002 Inverurie Loco Works were elected into the HFL to give it a membership of 15 clubs. Inverurie Locos are another Highland League football club with its origins in the Scottish railways, having been formed by employees of the Great North of Scotland Railway who had their Locomotive and Carriage and Wagon Workshops in Inverurie, hence the football club's name.

In 2008, North Region Junior League sides Formartine United and Turriff United both submitted bids to join the Highland League, following in the footsteps of past Junior League side Inverurie Locos. Banks O' Dee and Strathspey Thistle also applied. On 25 February 2009, Formartine United, Strathspey Thistle and Turriff United were accepted into the league for the following season, with Banks O' Dee being the unsuccessful club.

Until the reorganisation of Scottish football during the 2012–13 season, the league was historically one of the senior leagues in Scottish football, along with the Scottish Premier League and Scottish Football League, as well as the East of Scotland and South of Scotland Leagues.

Since the 2014–15 season, the league champions have had the chance to qualify for promotion to the Scottish League Two via a play-off with the winners of the Lowland Football League, the winners then playing off against the bottom team in League Two. Although the introduction of a route into the Scottish Professional Football League was broadly welcomed, it also provoked some concern about the potential financial burden on smaller clubs who may need to significantly upgrade their grounds to meet the required standards. The logistics of travel to away games in a league dominated by central belt teams is also a concern, particularly for geographically remote clubs such as Wick Academy and Brora Rangers.

At the end of the 2018–19 season, Cove Rangers became the first Highland League club to gain promotion to the SPFL via the pyramid play-off, after beating Berwick Rangers 7–0 on aggregate in the League Two play-off final. Two years later, Brechin City became the first SPFL club to be relegated into the Highland League after losing 3–1 on aggregate to Kelty Hearts in the League Two play-off final.

At the end of the 2020–21 season the threat of relegation was introduced to the league, as the North Caledonian League, a newly formed Midlands League, and North Superleague were all brought into the pyramid as feeder leagues. At the end of the following season, Fort William became the first victim of the drop as they failed to play their games against North Superleague side Banks O' Dee in the playoff final, giving the Aberdeen side a bye into the Highland League as Fort William fell into the North Caledonian League.