The Fife Cup has six participants – the four SPFL clubs based in the Kingdom of Fife plus East of Scotland League side Burntisland Shipyard and Kelty Hearts of the Lowland League. Kelty are making their debut this season after becoming the first new Fife FA member in many years.
Burntisland Shipyard are defending the trophy they won for the first time ever in 2017-18.
- Burntisland Shipyard 1-2 Cowdenbeath (@ Central Park, Nov 15)
- Kelty Hearts 1-5 Raith Rovers (Dec 18)
- Cowdenbeath 1-2 East Fife (Apr 2)
- Raith Rovers 1-2 Dunfermline Athletic (Apr 30)
- Dunfermline Athletic 3-0 East Fife (@ East End Park, Aug 27) – att 400