29th August, 2026
- Balgonie Scotia - Benarty Astros
- Bridge of Earn - Cupar Hearts
- Burntisland United - Leslie Hearts
- Kinross Colts - Fife Thistle
- Kirkcaldy/Dysart YMCA - The Swifts
- Lochgelly United - Leven United
- Pittenweem Rovers - Greig Park Rangers
25th August, 2026
- Benarty Astros - Leslie Hearts
- Cupar Hearts - Fife Thistle
- Greig Park Rangers - Kinross Colts
- Leven United - Balgonie Scotia
- Lochgelly United - Pittenweem Rovers
- Markinch - Burntisland United
- The Swifts - Bridge of Earn
22nd August, 2026
- Balgonie Scotia - The Swifts
- Bridge of Earn - Lochgelly United
- Burntisland United - Leven United
- Fife Thistle - Greig Park Rangers
- Kinross Colts - Markinch
- Kirkcaldy/Dysart YMCA - Benarty Astros
- Leslie Hearts - Cupar Hearts
18th August, 2026
- Cupar Hearts - Benarty Astros
- Greig Park Rangers - Leslie Hearts
- Leven United - Kinross Colts
- Lochgelly United - Balgonie Scotia
- Markinch - Fife Thistle
- Pittenweem Rovers - Kirkcaldy/Dysart YMCA
- The Swifts - Burntisland United
15th August, 2026
- Balgonie Scotia - Markinch
- Benarty Astros - Greig Park Rangers
- Burntisland United - Lochgelly United
- Fife Thistle - Leven United
- Kinross Colts - The Swifts
- Kirkcaldy/Dysart YMCA - Cupar Hearts
- Pittenweem Rovers - Bridge of Earn
