1st Round Weekend 7th / 8th September 2019 no extra time ties go straight to penalties
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| Arniston Rangers YFC v Bathgate Thistle CFC |
6-2 |
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| Alpha BC v Beechwood FC |
2-1 |
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| Linlithgow Rose Maroon v Spartans FC Youth |
0-7 |
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| Gartcairn FA v Edinburgh City FC |
0-10 |
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| Arniston Rangers Blues v Edinburgh City Whites |
0-1 |
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| Broxburn Athletic Colts United v Edinburgh City Blacks |
2-4 |
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2nd Round Weekend 5th / 6th October 2019
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| 1 Edinburgh South CFC Colts v Spartans FC Reds |
0-9 |
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| 2 Civil Service Strollers v Blackburn United |
4-5 |
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| 3 Tynecastle FC v Edinburgh South CFC Reds |
6-0 |
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| 4 Musselburgh Young Stars v Newtongrange Star YDA |
2-3 |
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| 5 Leith Athletic Blacks v Broxburn Diamonds |
0-1 |
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| 6 Bonnyrigg Rose Cobras v Gala Fairydean Rovers |
0-1 |
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| 7 Musselburgh Windsor FC v East Calder CFC |
1-0 |
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| 8 Edinburgh City Whites v Edinburgh South CFC |
4-1 |
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| 9 Tranent Colts FC v Hutchison Vale FC |
0-3 |
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| 10 Leith Athletic FC v Salvesen CFC |
1-0 |
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| 11 Murieston United Blues v Portobello CFA |
1-4 |
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| 12 Alpha BC v Spartans FC Youth |
4-0 |
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| 13 Kirkfield United v Linlithgow Rose CFC |
4-1 |
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| 14 Dimsdale Juniors v Arniston Rangers YFC |
0-1 |
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| 15 Currie Star FC v Edinburgh City FC |
0-4 |
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| 16 Edinburgh City Blacks v Longniddry Villa |
3-1 |
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3rd Round Weekend 9th / 10th November 2019
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| 1 Arniston Rangers YFC v Musselburgh Windsor FC |
1-8 |
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| 2 Edinburgh City FC v Broxburn Diamonds |
2-2 6-5p |
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| 3 Spartans FC Reds v Portobello CFA |
9-0 |
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| 4 Edinburgh City Blacks v Leith Athletic FC |
2-0 |
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| 5 Alpha BC v Kirkfield United |
0-2 |
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| 6 Hutchison Vale FC v Tynecastle FC |
0-3 |
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| 7 Edinburgh City Whites v Newtongrange Star |
6-2 |
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| 8 Gala Fairydean Rovers v Blackburn United |
3-2 |
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4th Round Weekend 23rd / 24th November 2019
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| 1 Edinburgh City Blacks v Gala Fairydean Rovers |
9-1 |
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| 2 Edinburgh City FC v Tynecastle FC |
0-8 |
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| 3 Spartans FC Reds v Musselburgh Windsor FC |
3-0 |
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| 4 Edinburgh City Whites v Kirkfield United |
1-0 |
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Semi finals Weekend 22nd / 23rd February 2020
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| 1 Edinburgh City Whites v Edinburgh City Blacks |
1-3 |
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| 2 Spartans FC Reds v Tynecastle FC |
1-0 |
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Final Saturday 30th May 2020
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| Edinburgh City Blacks v Spartans FC Reds |
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