The Fife Cup now has eight participants – the four SPFL clubs based in the Kingdom of Fife, Kelty Hearts of the Lowland League plus East of Scotland League side Burntisland Shipyard, Dundonald Bluebell and Hill of Beath Hawthorn.
Dundonald and Hill of Beath are new entrants this year, after they joined in the Fife FA in May 2019.
In October 2019, it was confirmed that Edinburgh based football retailer Football Nation would sponsor the competition.
- Burntisland Shipyard 0-4 Raith Rovers (Aug 20)
- Cowdenbeath 4-0 Kelty Hearts (Oct 8)
- Dundonald Bluebell – East Fife (Oct 28 @ New Bayview, post Oct 15)
- Dunfermline Athletic – Hill of Beath Hawthorn (Nov 19)