29th August, 2026
- Auchtermuchty Bellvue - Methilhill Strollers
- Dunfermline City - Kingdom of Fife Thistle
- Eastvale - Inverkeithing United
- Kennoway - Pitreavie United
- Leven - St Monans Swallows
- Newport - Kettle United
25th August, 2026
- Inverkeithing United - Auchtermuchty Bellvue
- Kettle United - Eastvale
- Kingdom of Fife Thistle - Leven
- Pitreavie United - Newport
- St Andrews Amateurs - Dunfermline City
- St Monans Swallows - Kennoway
22nd August, 2026
- Auchtermuchty Bellvue - Kettle United
- Eastvale - Pitreavie United
- Kennoway - Kingdom of Fife Thistle
- Leven - St Andrews Amateurs
- Methilhill Strollers - Inverkeithing United
- Newport - St Monans Swallows
18th August, 2026
- Dunfermline City - Leven
- Kettle United - Methilhill Strollers
- Kingdom of Fife Thistle - Newport
- Pitreavie United - Auchtermuchty Bellvue
- St Andrews Amateurs - Kennoway
- St Monans Swallows - Eastvale
15th August, 2026
- Auchtermuchty Bellvue 3 - 2 St Monans Swallows
- Eastvale 2 - 0 Kingdom of Fife Thistle
- Inverkeithing United 1 - 2 Kettle United
- Kennoway 5 - 0 Dunfermline City
- Methilhill Strollers 2 - 2 Pitreavie United
- Newport 1 - 1 St Andrews Amateurs
