| Saturday 13th August 2011 |
| Home | | | Away | Competition |
| Rosyth Civil Service | 5 | 1 | Balgonie Scotia 1896 | Kingdom Caledonian League |
| Bowhill Rovers | P | P | Burntisland Shipyard | Kingdom Caledonian League |
| Cupar Hearts | P | P | Eastvale | Kingdom Caledonian League |
| Leven United | 3 | 0 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| Star Hearts | P | P | Kinross | Kingdom Caledonian League |
| Kettle United | 2 | 4 | Lumphinnans United | Kingdom Caledonian League |
| Fair City | 2 | 1 | Strathmiglo United | Kingdom Caledonian League |
| |
| Tuesday 16th August 2011 |
| Home | | | Away | Competition |
| Inverkeithing Hillfield Swifts | 3 | 0 | Bowhill Rovers | Kingdom Caledonian League |
| Balgonie Scotia 1896 | 1 | 4 | Cupar Hearts | Kingdom Caledonian League |
| Burntisland Shipyard | 3 | 0 | Fair City | Kingdom Caledonian League |
| Kinross | 2 | 3 | Kettle United | Kingdom Caledonian League |
| Eastvale | P | P | Leven United | Kingdom Caledonian League |
| Lumphinnans United | 1 | 1 | Rosyth Civil Service | Kingdom Caledonian League |
| Strathmiglo United | 4 | 1 | Star Hearts | Kingdom Caledonian League |
| |
| Saturday 20th August 2011 |
| Home | | | Away | Competition |
| Fair City | 3 | 1 | Bowhill Rovers | Kingdom Caledonian League |
| Leven United | 5 | 2 | Burntisland Shpyard | Kingdom Caledonian League |
| Balgonie Scotia 1896 | 1 | 5 | Eastvale | Kingdom Caledonian League |
| Star Hearts | 2 | 4 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| Rosyth Civil Service | 7 | 1 | Kinross | Kingdom Caledonian League |
| Cupar Hearts | 4 | 2 | Lumphinnans United | Kingdom Caledonian League |
| Kettle United | A | A | Strathmiglo United | Kingdom Caledonian League |
| |
| Tuesday 23rd August 2011 |
| Home | | | Away | Competition |
| Kinross | 1 | 4 | Balgonie Scotia 1896 | Kingdom Caledonian League |
| Inverkeithing Hillfield Swifts | 2 | 8 | Cupar Hearts | Kingdom Caledonian League |
| Strathmiglo United | 3 | 3 | Eastvale | Kingdom Caledonian League |
| Burntisland Shipyard | 3 | 1 | Kettle United | Kingdom Caledonian League |
| Fair City | 1 | 4 | Leven United | Kingdom Caledonian League |
| Bowhill Rovers | 1 | 5 | Rosyth Civil Service | Kingdom Caledonian League |
| Lumphinnans United | 8 | 0 | Star Hearts | Kingdom Caledonian League |
| |
| Saturday 27th August 2011 |
| Home | | | Away | Competition |
| Kettle United | 0 | 3 | Bowhill Rovers | Kingdom Caledonian League |
| Star Hearts | 0 | 2 | Burntisland Shipyard | Kingdom Caledonian League |
| Rosyth Civil Service | 5 | 1 | Fair City | Kingdom Caledonian League |
| Balgonie Scotia 1896 | 7 | 2 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| Eastvale | 10 | 0 | Kinross | Kingdom Caledonian League |
| Leven United | 3 | 2 | Lumphinnans United | Kingdom Caledonian League |
| Cupar Hearts | 1 | 0 | Strathmiglo United | Kingdom Caledonian League |
| |
| Tuesday 30th August 2011 |
| Home | | | Away | Competition |
| Lumphinnans United | 4 | 0 | Balgonie Scotia 1896 | Kingdom Caledonian League |
| Fair City | 0 | 2 | Cupar Hearts | Kingdom Caledonian League |
| Burntisland Shipyard | 0 | 3 | Eastvale | Kingdom Caledonian League |
| Kinross | 1 | 5 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| Bowhill Rovers | 1 | 4 | Leven United | Kingdom Caledonian League |
| Strathmiglo United | 2 | 2 | Rosyth Civil Service | Kingdom Caledonian League |
| Kettle United | 3 | 1 | Star Hearts | Kingdom Caledonian League |
| |
| Saturday 3rd September 2011 |
| Home | | | Away | Competition |
| Lumphinnans United | 4 | 0 | Star Hearts | M+H Engineering League Cup 1st round |
| Cupar Hearts | 0 | 1 | Rosyth Civil Service | M+H Engineering League Cup 1st round |
| Kettle United | 6 | 0 | Eastvale | M+H Engineering League Cup 1st round |
| Strathmiglo United | 6 | 6 | Bowhill Rovers (won on pens) | M+H Engineering League Cup 1st round |
| Leven United | 6 | 0 | Kinross | Kingdom Caledonian League |
| Burntisland Shipyard | 0 | 6 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| |
| Saturday 10th September 2011 |
| Home | | | Away | Competition |
| Inverkeithing Hillfield Swifts | 5 | 1 | Balgonie Scotia 1896 | M+H Engineering League Cup 1st round |
| Fair City | 1 | 2 | Burntisland Shipyard | M+H Engineering League Cup 1st round |
| Lumphinnans United | 11 | 1 | Kinross | M+H Engineering League Cup 2nd round |
| Bowhill Rovers | 1 | 1 | Kettle United | M+H Engineering League Cup 2nd round |
| Rosyth Civil Service | P | P | Leven United | M+H Engineering League Cup 2nd round |
| Eastvale | 1 | 2 | Cupar Hearts | Kingdom Caledonian League |
| |
| Saturday 17th September 2011 |
| Home | | | Away | Competition |
| Rosyth Civil Service | 3 | 1 | Leven United | M+H Engineering League Cup 2nd round |
| Inverkeithing Hillfield Swifts | 3 | 0 | Burntisland Shipyard | M+H Engineering League Cup 2nd round |
| Balgonie Scotia 1896 | 4 | 2 | Kettle United | Kingdom Caledonian League |
| Eastvale | 3 | 1 | Fair City | Kingdom Caledonian League |
| Kinross | 1 | 9 | Strathmiglo United | Kingdom Caledonian League |
| Lumphinnans United | 2 | 0 | Bowhill Rovers | Kingdom Caledonian League |
| Star Hearts | 2 | 3 | Cupar Hearts | Kingdom Caledonian League |
| |
| Saturday 24th September 2011 |
| Home | | | Away | Competition |
| Culter | 4 | 0 | Burntisland Shipyard | Scottish Cup 1st round |
| Balgonie Scotia 1896 | 0 | 2 | Hawick Waverley | Scottish Cup 1st round |
| Camelon Albion | 2 | 1 | Strathmiglo United | Scottish Cup 1st round |
| Hillfoot Community | 2 | 9 | Eastvale | Scottish Cup 1st round |
| Lumphinnans United | 10 | 0 | Newburgh | Scottish Cup 1st round |
| Bowhill Rovers | 1 | 5 | Cupar Hearts | Kingdom Caledonian League |
| Star Hearts | 1 | 3 | Fair City | Kingdom Caledonian League |
| Kettle United | 0 | 3 | Leven United | Kingdom Caledonian League |
| Inverkeithing Hillfield Swifts | 1 | 4 | Rosyth Civil Service | Kingdom Caledonian League |
| |
| Saturday 8th October 2011 |
| Home | | | Away | Competition |
| NCR | 0 | 1 | Fair City | North of Tay Cup 2nd round |
| Kinross | 1 | 5 | Burrelton Rovers | North of Tay Cup 2nd round |
| Bowhill Rovers | 1 | 0 | Balgonie Scotia 1896 | Kingdom Caledonian League |
| Cupar Hearts | 2 | 1 | Rosyth Civil Service | Kingdom Caledonian League |
| Inverkeithing Hillfield Swifts | 0 | 3 | Eastvale | Kingdom Caledonian League |
| Lumphinnans United | 3 | 0 | Burntisland Shipyard | Kingdom Caledonian League |
| Star Hearts | 1 | 9 | Leven United | Kingdom Caledonian League |
| Strathmiglo United | 7 | 1 | Kettle United | Kingdom Caledonian League |
| |
| Saturday 15th October 2011 |
| Home | | | Away | Competition |
| Star Hearts | 0 | 5 | Rosyth Civil Service | Scottish Cup 2nd round |
| Bowhill Rovers | 3 | 2 | Kirkcaldy YMCA | Scottish Cup 2nd round |
| Cupar Hearts | 6 | 0 | Callender Thistle | Scottish Cup 2nd round |
| Dalgety Bay | 1 | 1 | Kinross | Scottish Cup 2nd round |
| Eastvale | 5 | 2 | Redpath Albion | Scottish Cup 2nd round |
| Inverkeithing Hillfield Swifts | 0 | 6 | Lumphinnans United | Scottish Cup 2nd round |
| Kettle United | 2 | 0 | Stirling Thistle | Scottish Cup 2nd round |
| Musselburgh Windsor | 0 | 8 | Leven United | Scottish Cup 2nd round |
| Milton Amateurs | 2 | 3 | Fair City | Scottish Cup 2nd round |
| Strathmiglo United | 4 | 1 | Balgonie Scotia 1896 | Kingdom Caledonian League |
| Burntisland Shipyard | 1 | 3 | Edinburgh City | South Scotland Challenge Cup 2nd round |
| |
| Saturday 22nd October 2011 |
| Home | | | Away | Competition |
| Burntisland Shipyard | 4 | 2 | Cabrea Athletic | Scottish Cup 2nd round |
| Kinross | 4 | 5 | Dalgety Bay | Scottish Cup 2nd round replay |
| Cupar Hearts | 3 | 0 | Comrie Tavern | Fife Cup 1st round |
| FC Bayside | 3 | 7 | Balgonie Scotia 1896 | Fife Cup 1st round |
| Kettle United | 2 | 5 | Kennoway Amateurs | Fife Cup 1st round |
| Bowhill Rovers | 6 | 3 | Hill of Beath Ramblers | Fife Cup 1st round |
| Lumphinnans United | 5 | 2 | Freuchie Amateurs | Fife Cup 1st round |
| Rosyth Wanderers | 4 | 0 | Inverkeithing Hillfield Swifts | Fife Cup 1st round |
| Rosyth Civil Service | 6 | 2 | St Andrews Amateurs | Fife Cup 1st round |
| Fair City | 4 | 1 | Star Hearts | Kingdom Caledonian League |
| Leven United | 4 | 2 | Strathmiglo United | Kingdom Caledonian League |
| |
| Saturday 22nd October 2011 |
| Home | | | Away | Competition |
| Kirkcaldy Rovers | 0 | 6 | Eastvale | Fife Cup 1st round |
| Dysart | 1 | 2 | Burntisland Shipyard | Fife Cup 1st round |
| Balgonie Scotia 1896 | 1 | 2 | Fair City | Kingdom Caledonian League |
| Bowhill Rovers | P | P | Kinross | Kingdom Caledonian League |
| Cupar Hearts | 1 | 1 | Leven United | Kingdom Caledonian League |
| Inverkeithing Hillfield Swifts | 0 | 3 | Strathmiglo United | Kingdom Caledonian League |
| Rosyth Civil Service | 4 | 0 | Star Hearts | Kingdom Caledonian League |
| |
| Sunday 30th October 2011. |
| Home | | | Away | Competition |
| Kettle United | 1 | 6 | Lumphinnans United | M+H Engineering League Cup Final |
| |
| Saturday 5th November 2011 |
| Home | | | Away | Competition |
| Braehead | 0 | 0 | Burntisland Shipyard | Scottish Cup 3rd round |
Eastvale
| 7 | 1 | Broomhill | Scottish Cup 3rd round |
| Glasgow University | 2 | 0 | Cupar Hearts | Scottish Cup 3rd round |
| Leven United | 2 | 2 | Dunipace Thistle | Scottish Cup 3rd round |
| Lumphinnans United | P | P | Ashfield Vics | Scottish Cup 3rd round |
| Stoneywood | 1 | 3 | Fair City | Scottish Cup 3rd round |
| Wellhouse | 4 | 2 | Rosyth Civil Service | Scottish Cup 3rd round |
| Bowhill Rovers | 5 | 2 | Glenmuir Thistle | Scottish Cup 3rd round |
| Balgonie Scotia 1896 | 2 | 1 | Inverkeithing Hillfield Swifts | Kingdom Caledonian League |
| Strathmiglo United | 2 | 0 | Kinross | Kingdom Caledonian League |
| Star Hearts | 0 |
