Matches are contested between any two SPFL clubs from Dunfermline Athletic, Raith Rovers (based in Kirkcaldy), East Fife (representing the Levenmouth area) and Cowdenbeath.

[12] Perhaps the most important Fife derby meeting of the early 21st century came a month after the Raith cup win, when Cowdenbeath overcame Dunfermline 4–1 on aggregate in the 2013–14 Championship play-off final to preserve their status in Scotland's second tier at their neighbours' expense.

[13] Dunfermline Athletic had their first sellout crowd in 15 years for a Fife derby played against First Division title rivals Raith Rovers in April 2011.

In 2017 Kelty left the Juniors and joined the East of Scotland League (which is part of the senior pyramid) with the aim of rising through the divisions and becoming an SPFL club.

[20] With the exception of Tayport who compete against teams in the Tayside area due to their proximity to Dundee via the Tay Road Bridge, the remainder of the Fife Junior clubs—Kennoway Star Hearts, Kirkcaldy & Dysart, Lochgelly Albert, Lochore Welfare, Newburgh, Rosyth, and Thornton Hibs—moved across to the East of Scotland League for the 2020–21 season.