1st Round Weekend 7th / 8th September 2019 no extra time ties go straight to penalties
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| Linlithgow Rose CFC v Linlithgow Rose Maroon |
9-0 |
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| Carluke United v Blackburn United |
4-2 |
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| Edinburgh City Whites v Tranent Colts FC |
3-1 |
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2nd Round Weekend 5th / 6th October
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| 1 West Lothian FC v Salvesen Vikings |
1-4 |
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| 2 Salvesen Blades v Gala Faiydean Rovers |
2-1 |
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| 3 North Merchiston Whites v Broxburn Athletic Colts |
1-7 |
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| 4 Edinburgh City FC v Murieston United Blues |
5-1 |
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| 5 Livingston FCCC Yellows v Pumpherston United |
10-1 |
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| 6 Murieston United Reds v Shotts YMCA |
0-1 |
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| 7 Craigroyston CYFC v Linlithgow Rose CFC |
1-0 |
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| 8 Peebles FC v Currie FC |
0-1 |
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| 9 Fauldhouse United v Craigshill CSC |
6-0 |
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| 10 Lothian Colts FC v Lothian Colts Blues |
9-0 |
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| 11 Spartans FC Whites v Eyemouth United FC Juniors |
0-9 |
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| 12 Leith Athletic Colts v Longniddry Villa |
3-2 |
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| 13 Livingston FC Reds v Musselburgh Young Stars |
8-0 |
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| 14 Bonnyrigg Rose Whites v Leith Athletic FC |
1-9 |
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| 15 Arniston Rangers YFC v Linlithgow Rose Whites |
1-0 |
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| 16 Gartcairn United v Newtongrange Star YDA |
9-0 |
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| 17 Whitburn FCA v Edinburgh South CFC |
0-9 |
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| 18 Armadale CFC v Hutchison Vale FC |
0-6 |
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| 19 Kirkfield United v Redhall Star YFC |
10-0 |
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| 20 Currie Star Blues v Tynecastle FC |
1-6 |
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| 21 Airdrie United v Armadale Blues |
9-0 |
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| 22 Spartans FC Reds v Dunbar United Colts |
5-1 |
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| 23 Cramond FC v Dalkeith Thistle CFC |
0-1 |
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| 24 Clelland BC v Inverkeithing United |
1-7 |
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| 25 Musselburgh Windsor FC v Haddington Athletic CFC |
6-0 |
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| 26 AC Rovers FC v Spartans FC Youth |
0-4 |
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| 27 Livingston FCC Blacks v Currie Star Whites |
10-0 |
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| 28 Carluke United v Penicuik Athletic YFC |
1-0 |
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| 29 Tynecastle FC Whites v Currie Star FC |
1-5 |
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| 30 Edinburgh United v Falkirk FCF |
4-3 |
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| 31 North Merchiston FC v Tranent Colts Blues |
9-1 |
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| 32 Portobello CFA v Edinburgh City Whites |
1-0 |
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3rd Round Weekend 9th / 10th November 2019
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| 1 Livingston FCC Blacks v Edinburgh City FC |
6-4 |
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| 2 Airdrie United BC v Carluke United |
1-0 |
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| 3 Leith Athletic Colts v North Merchiston FC |
2-4 |
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| 4 Fauldhouse United v Salvesen Vikings |
0-1 |
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| 5 Edinburgh United v Craigroyston CYFC |
2-5 |
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| 6 Hutchison Vale FC v Shotts YMCA |
1-0 |
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| 7 Eyemouth United FC v Tynecastle FC |
0-9 |
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| 8 Lothian Colts FC v Musselburgh Windsor FC |
5-1 |
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| 9 Spartans FC Youth v Currie FC |
6-0 |
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| 10 Livingston FCC Yellows v Broxburn Athletic Colts |
10-1 |
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| 11 Dalkeith Thistle CFC v Edinburgh South CFC |
4-5 |
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| 12 Leith Athletic FC v Kirkfield United |
10-3 |
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| 13 Arniston Rangers YFC v Livingston FC Reds |
0-8 |
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| 14 Salvesen Blades v Gartcairn United |
0-0 3-2p |
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| 15 Inverkeithing United v Spartans FC Reds |
7-1 |
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| 16 Currie Star FC v Portobello CFA |
1-5 |
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4th Round Weekend 23rd /24th November 2019
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| 1 Leith Athletic FC v Livingston FCC Blacks |
3-5 |
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| 2 Portobello CFA v Spartans FC Youth |
5-0 |
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| 3 Hutchison Vale FC v Edinburgh South CFC |
2-1 |
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| 4 Craigroyston CYFC v Livingston FCC Yellows |
3-7 |
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| 5 Salvesen Blades v Livingston FC Reds |
4-4 4-2p |
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| 6 Lothian Colts FC v Tynecastle FC |
1-7 |
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| 7 Salvesen Vikings v North Merchiston FC |
9-0 |
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| 8 Airdrie United BC v Inverkeithing United |
2-3 |
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5th Round Weekend 14th / 15th December 2019
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| 1 Livingston FCC Yellows v Portobello CFA |
0-9 |
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| 2 Inverkeithing United v Tynecastle FC |
4-2 |
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| 3 Salvesen Blades v Hutchison Vale FC |
1-4 |
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| 4 Livingston FCC Blacks v Salvesen Vikings |
0-4 |
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Semi finals Weekend 22nd / 23rd February 2020
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| 1 Salvesen Vikings v Portobello CFA |
0-6 |
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| 2 Inverkeithing United v Hutchison Vale FC |
2-0 |
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Final Sunday 31st May 2020
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| Portobello CFA v Inverkeithing United |
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