1st Round Weekend 7th / 8th September 2019 no extra time ties go straight to penalties
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| Loanhead MYFC v Currie FC Colts |
0-6 |
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| Leith Athletic Colts v Edinburgh City Colts |
2-2 2-4p |
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| Musselburgh Windsor FC v Edinburgh South CFC |
9-0 |
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| Newcraighall Leith Vics v AC Rovers FC |
2-4 |
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| Eyemoth United FC Juniors v Linlithgow Rose CFC |
2-1 |
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| St Bernard's BC Midlothian v Hillfield Swifts |
2-5 |
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| Bathgate Thistle CFC Rovers v Leith Athletic |
1-1 2-4p |
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| Redhall Star YFC v Tynecastle FC |
0-9 |
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| Spartans FC Youth v West Calder United |
10-1 |
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| Broxburn Athletic Colts United v Longniddry Villa |
1-6 |
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| Edinburgh South CFC Reds v Gala Fairydean Rovers |
2-8 |
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| Kirkfield United v Dunbar United Colts |
3-2 |
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| Edinburgh United v Edinburgh City FC |
2-0 |
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| Currie Star FC v Longniddry Villa Colts |
2-2 4-5p |
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| Whitburn Claret & Amber v Musselburgh Young Stars |
5-4 |
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| Bathgate Juniors v Peebles FC Athletic |
2-0 |
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2nd Round Weekend 5th / 6th October 2019
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| 1 Murieston United Blues v Longniddry Villa Colts |
3-0 |
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| 2 Peebles FC v Currie FC Colts |
8-0 |
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| 3 Hutchison Vale Colts v Whitburn Claret & Amber |
10-0 |
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| 4 Bonnyrigg Rose Whites v Eyemouth United FC Juniors |
1-3 |
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| 5 Armadale Thistle v Broxburn Athletic Colts |
0-7 |
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| 6 Edinburgh United v Gala Fairydean Rovers |
4-0 |
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| 7 Currie FC v Edinburgh City Colts |
3-0 |
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| 8 Kirkfield United v Longniddry Villa |
3-2 |
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| 9 Spartans FC Youth v Craigroyston CYFC |
9-1 |
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| 10 Linlithgow Rose Maroon v Newmains Hammers |
3-0 |
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| 11 Cragshill Thistle v Penicuik Athletic YFC |
7-2 |
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| 12 Bathgate Juniors v Leith Athletic FC |
0-10 |
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| 13 Livingston Yellows v Beechwood FC |
5-2 |
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| 14 Hutchison Vale FC v Musselburgh Windsor FC |
4-0 |
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| 15 Arniston Rangers YFC v Hillfield Swifts |
1-5 |
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| 16 Tynecastle FC v AC Rovers FC |
4-1 |
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3rd Round 9th / 10th Novemver 2019
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| 1 Spartans FC Youth v Peebles FC |
9-2 |
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| 2 Murieston United Blues v Broxburn Athletic Colts |
5-1 |
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| 3 Tynecastle FC v Hutchison Vale FC |
2-1 |
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| 4 Currie FC v Edinburgh United |
0-5 |
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| 5 Eyemouth United FC v Linlithgow Rose Maroon |
1-0 |
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| 6 Craigshill Thistle v Kirkfield United |
1-7 |
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| 7 Hutchison Vale Colts v Livingston Yellows |
4-0 |
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| 8 Hillfield Swifts v Leith Athletic FC |
0-1 |
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4th Round Weekend 23rd / 24th November 2019
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| 1 Kirkfield United v Eyemouth United FC |
7-0 |
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| 2 Murieston United Blues v Tynecastle FC |
1-4 |
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| 3 Spartans FC Youth v Edinburgh United |
3-0 |
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| 4 Hutchison Vale Colts v Leith Athletic FC |
1-1 5-4p |
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Semi finals Weekend 22nd / 23rd February 2020
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| 1 Tynecastle FC v Hutchison Vale Colts |
1-0 |
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| 2 Spartans FC Youth v Kirkfield United |
4-0 |
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Final Saturday 30th May 2020
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| Tynecastle FC v Spartans FC Youth |
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