Saturday 12th September 2020
Cupar Hearts 4-0 Crossgates Primrose FC
⚽️ Callum Hutchinson
⚽️ Jamie Leslie
⚽️ Richie Lawson
⚽️ Ryan Buchan

Tuesday 15th September 2020
Cupar Hearts 5-0 Rosyth FC
⚽️ Gary Reilly
⚽️ Barry Sibanda
⚽️ Aaron Anderson
⚽️ Richie Lawson
⚽️ Kyle Baker

Saturday 19th September 2020
Leven United 1-2 Cupar Hearts
⚽️⚽️ Jamie Leslie

Tuesday 22nd September 2020
Cupar Hearts 3-2 Glenrothes FC
⚽️ Scott McBride
⚽️ Kyle Baker
⚽️ Greg Honeyman

Saturday 26th September 2020
Kennoway Star Hearts 1-4 Cupar Hearts
⚽️ Kyle Baker
⚽️⚽️ Barry Sibanda
⚽️ Richie Lawson

Tuesday 29th September 2020
Cupar Hearts 7-0 St Andrews Utd
⚽️ Aaron Anderson
⚽️⚽️ Barry Sibanda
⚽️⚽️ Scott McBride
⚽️ Richie Lawson
⚽️ Cameron Greenhill