26th September, 2026
- Burntisland United - Benarty Astros
- Fife Thistle - Balgonie Scotia
- Kinross Colts - Bridge of Earn
- Kirkcaldy/Dysart YMCA - Pittenweem Rovers
- Leven United - Markinch
- Lochgelly United - Cupar Hearts
- The Swifts - Greig Park Rangers
19th September, 2026
- Balgonie Scotia 2 - 6 Cupar Hearts
- Benarty Astros 1 - 6 Markinch
- Bridge of Earn 0 - 4 Greig Park Rangers
- Kinross Colts 0 - 4 The Swifts
- Kirkcaldy/Dysart YMCA 1 - 0 Burntisland United
- Leven United 1 - 1 Lochgelly United
15th September, 2026
- Cupar Hearts 6 - 0 Kinross Colts
12th September, 2026
- Benarty Astros 1 - 2 The Swifts
- Greig Park Rangers 4 - 0 Kirkcaldy/Dysart YMCA
- Leven United 5 - 0 Balgonie Scotia
- Lochgelly United 2 - 1 Pittenweem Rovers
- Markinch 9 - 0 Fife Thistle
5th September, 2026
- Greig Park Rangers 8 - 0 Kinross Colts
29th August, 2026
- Bridge of Earn 4 - 1 Benarty Astros
- Burntisland United 0 - 4 Cupar Hearts
- Kirkcaldy/Dysart YMCA 2 - 0 Fife Thistle
- Pittenweem Rovers 0 - 8 Leven United
- The Swifts 0 - 2 Lochgelly United
22nd August, 2026
- Cupar Hearts 8 - 0 Benarty Astros
- Fife Thistle 0 - 7 Greig Park Rangers
- Lochgelly United 2 - 3 Kirkcaldy/Dysart YMCA
- Markinch 5 - 0 Burntisland United
- The Swifts 1 - 1 Bridge of Earn
15th August, 2026
- Balgonie Scotia - Markinch
- Benarty Astros 2 - 9 Greig Park Rangers
- Burntisland United 1 - 2 Lochgelly United
- Fife Thistle 0 - 10 Leven United
- Kirkcaldy/Dysart YMCA 0 - 8 Cupar Hearts
- Pittenweem Rovers 1 - 1 Bridge of Earn
