1st Round Weekend 7th / 8th September 2019 no extra time ties go straight to penalties
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| Bonnyrigg Rose Reds v Gala Fairydean Rovers |
0-1 |
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| Salvesen CFC v Edina Hibs |
1-0 |
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| Spartans FC Youth v Edinburgh South CFC |
6-4 |
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| Salvesen Reds v Hutchison Vale FC |
0-1 |
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| Edinburgh City Reds v Haddington Athletic Colts |
2-1 |
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| Tranent Colts FC v Leith Athletic FC |
3-5 |
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| Lothian Colts FC v Ancrum JFC |
0-1 |
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| Civil Service Strollers v Spartans FC Whites |
0-9 |
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| Salvesen Blues v Lasswade Thistle Reds |
1-1 4-3p |
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| North Berwick FC v Edinburgh South CFC Raccoons |
7-5 |
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| Murieston United Blues v Broxburn Athletic Colts |
9-1 |
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| Edinburgh City FC v Edinburgh United |
10-1 |
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2nd Round 5th / 6th October 2019
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| 1 AC Oxgangs Reds v Musselburgh Young Stars |
8-3 |
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| 2 Armadale CFC United v Linlithgow Rose Maroons |
7-0 |
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| 3 Nova Star v Musselburgh Windsor Blues |
9-0 |
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| 4 Livingson FC Lions v Bonnyrigg Rose Whites |
0-6 |
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| 5 Arniston Rangers YFC v Bathgate Thistle Blues |
2-8 |
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| 6 Arniston Rangers Reds v Salvesen Blues |
0-1 |
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| 7 Murieston United Blue v Edinburgh South CFC Bocas |
1-0 |
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| 8 Lochend FA v Spartans FC Whites |
4-1 |
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| 9 Gartcairn FA Whites v Bathgate Thistle Whites |
5-1 |
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| 10 Bonnyrigg Rose FC v Hillfield Swifts Jets |
1-6 |
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| 11 Linlithgow Rose CFC v Livingston CFC Yellows |
8-3 |
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| 12 Dunbar United Colts v Kirkfield United |
1-10 |
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| 13 Musselburgh Windsor FC v Craigroyston CYFC |
9-0 |
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| 14 Edinburgh South CFC Cobras v Edinburgh City FC |
1-0 |
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| 15 Redhall Star YFC v Tranent Colts Blues |
5-1 |
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| 16 Polbeth United v North Berwick FC |
0-5 |
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| 17 Edinburgh South CFC Athletico v Tynecastle FC |
3-1 |
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| 18 Blackburn United v Gala Fairydean Rovers |
9-0 |
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| 19 East Calder CFC v Salvesen CFC |
0-10 |
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| 20 Portobello CFA Thistle v Newtongrange Star YDA |
1-0 |
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| 21 Leith Athletic Colts v Haddington Athletic CFC Claret |
3-5 |
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| 22 Gartcairn FA Blues v Lauderdale FC |
3-7 |
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| 23 Edinburgh City Reds v Portobello CFA |
0-1 |
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| 24 Haddington Athletic CFC v Milton Rovers YFC |
3-2 |
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| 25 Dalkeith Thistle Cardo v Murieston Reds |
0-1 |
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| 26 Bathgate Thistle Blacks v Newcraighall Leith Vics |
1-0 |
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| 27 Dalkeith Thistle CFC v Edinburgh South CFC Wildcats |
9-0 |
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| 28 Lasswade Thistle FC v Craigshill Thistle CSC |
10-0 |
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| 29 Hutchison Vale FC v Leith Athletic FC |
9-1 |
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| 30 Currie Star Colts v Tynecastle FC Maroon |
0-1 |
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| 31 Penicuik Athletic YFC v Ancrum JFC |
3-5 |
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| 32 Lochend FC Colts v Spartans FC Youth |
0-9 |
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3rd Round 9th / 10th November 2019
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| 1 Lochend FA v Bonnyrigg Rose Whites |
0-9 |
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| 2 Lasswade Thistle FC v Linlithgow Rose CFC |
1-0 |
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| 3 Kirkfield United v Murieston United Reds |
4-6 |
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| 4 North Berwick FC v Nova Star |
1-9 |
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| 5 Edinburgh South Athletico v Haddington Athletic CFC |
1-3 |
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| 6 Musselburgh Windsor FC v Redhall Star YFC |
9-0 |
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| 7 Salvesen Blues v Spartans FC Youth |
0-9 |
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| 8 Haddington Athletic Claret v Murieston United Blue |
1-7 |
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| 9 Portobello CFA Thistle v Bathgate Thistle Blacks |
2-0 |
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| 10 AC Oxgangs Reds v Lauderdale FC |
1-5 |
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| 11 Edinburgh South Cobras v Dalkeith Thistle CFC |
0-9 |
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| 12 Tynecastle FC Maroon v Portobello CFA |
1-8 |
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| 13 Hillfield Swifts Jets v Blackbun United |
0-2 |
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| 14 Salvesen CFC v Hutchison Vale FC |
2-2 2-4p |
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| 15 Bathgate Thistle Blues v Ancrum FC |
9-3 |
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| 16 Armadale CFC United v Gartcairn FA Whites |
2-10 |
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4th Round 23rd / 24th November 2019
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| 1 Gartcairn FA Whites v Lauderdale FC |
9-0 |
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| 2 Portobello CFA Thistle v Nova Star |
3-6 |
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| 3 Dalkeith Thistle CFC v Lasswade Thistle FC |
1-6 |
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| 4 Portobello CFA v Murieston United Blue |
9-1 |
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| 5 Blackburn United v Bathgate Thistle Blues |
2-1 |
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| 6 Haddington Athletic CFC v Murieston United Reds |
2-1 |
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| 7 Spartans FC Youth v Bonnyrigg Rose Whites |
6-1 |
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| 8 Musselburgh Windsor FC v Hutchison Vale FC |
2-3 |
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5th Round 14th / 15th December 2019
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| 1 Hutchison Vale FC v Portobello CFA |
0-8 |
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| 2 Nova Star v Haddington Athletic CFC |
4-2 |
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| 3 Spartans FC Youth v Blackburn United |
3-3 3-5p |
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| 4 Lasswade Thistle v Gartcairn FA Whites |
5-1 |
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Semi finals 22nd / 23rd February 2020
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| 1 Lasswade Thistle FC v Blackburn United |
1-0 |
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| 2 Portobello CFA v Nova Star |
2-1 |
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Final Sunday 31st May 2020
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| Lasswade Thistle FC v Portobello CFA |
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