Saturday 21st July 2018.
Cupar Hearts 1-4 Crossgates Primrose
⚽️ Martin Woods (26)

Saturday 28th July 2018.
Lochgelly Albert 0-2 Cupar Hearts
⚽️ Steven Pennington (22)
⚽️ Jakub Dobes (70)

Tuesday 31st July 2018.
Cupar Hearts 3-0 Kennoway Ams
⚽️ Scott McKay (46)
⚽️ Ryan Gray (68)
⚽️ Dean Johnstone (85)

Saturday 4th August 2018.
Cupar Hearts 2-0 Barnhill
⚽️ Steven Pennington (33)
⚽️ Ryan Gray (77)

Tuesday 7th August 2018.
St Monans 2-1 Cupar Hearts
⚽️ Zac Deponio (37)