| Friday, 23rd August 2019 | ||||||
| Under 20 Conference A | ||||||
| 23 Aug 2019 Friday 8.00pm | Blackburn United | 6-0 | Hill of Beath Hawthorn | |||
| 23 Aug 2019 Friday 8.00pm | Bonnyrigg Rose | 2-6 | Dundonald Bluebell | |||
| 23 Aug 2019 Friday 8.00pm | East Fife | 4-1 | Dalkeith Thistle | |||
| 23 Aug 2019 Friday 8.00pm | Lothian Thistle Hutchison Vale | 1-2 | Edinburgh City | |||
| 23 Aug 2019 Friday 8.00pm | The Spartans | 1-0 | Edinburgh United | |||
| 23 Aug 2019 Friday 8.00pm | Tynecastle | 3-4 | Upper Annandale | |||
| Friday, 23rd August 2019 | ||||||
| Under 20 Conference B | ||||||
| 23 Aug 2019 Friday 7.30pm | Newtongrange Star | 3-4 | Musselburgh Athletic | |||
| 23 Aug 2019 Friday 7.45pm | Dunipace | 1-3 | Kelty Hearts | |||
| 23 Aug 2019 Friday 8.00pm | Broxburn Athletic | 0-0 | Inverkeithing Hillfield Swifts | |||
| 23 Aug 2019 Friday 8.00pm | Camelon Juniors | 1-3 | BSC Glasgow | |||
| 23 Aug 2019 Friday 8.00pm | Haddington Athletic | 2-3 | Civil Service Strollers | |||
| 23 Aug 2019 Friday 8.00pm | Mid Annandale | 3-1 | Preston Athletic | |||
| 23 Aug 2019 Friday 8.00pm | Penicuik Athletic | 3-2 | Bonnyton Thistle | |||
| Friday, 30th August 2019 | ||||||
| Under 20 Conference A | ||||||
| 30 Aug 2019 Friday 7.45pm | Cumbernauld Colts | 3-4 | Tynecastle | |||
| 30 Aug 2019 Friday 8.00pm | Dundonald Bluebell | 2-0 | Lothian Thistle Hutchison Vale | |||
| 30 Aug 2019 Friday 8.00pm | Edinburgh City | 8-1 | East Fife | |||
| 30 Aug 2019 Friday 8.00pm | Hill of Beath Hawthorn | 2-2 | Bonnyrigg Rose | |||
| 30 Aug 2019 Friday 8.00pm | Upper Annandale | 1-2 | The Spartans | |||
| Friday, 30th August 2019 | ||||||
| Under 20 Conference B | ||||||
| 30 Aug 2019 Friday 7.45pm | Camelon Juniors | 4-3 | Penicuik Athletic | |||
| 30 Aug 2019 Friday 7.45pm | Kelty Hearts | 4-0 | Mid Annandale | |||
| 30 Aug 2019 Friday 8.00pm | Bonnyton Thistle | 3-0 | Broxburn Athletic | |||
| 30 Aug 2019 Friday 8.00pm | Civil Service Strollers | 8-0 | Newtongrange Star | |||
| 30 Aug 2019 Friday 8.00pm | Inverkeithing Hillfield Swifts | 5-3 | Dunipace | |||
| 30 Aug 2019 Friday 8.00pm | Preston Athletic | 3-3 | Haddington Athletic | |||
| Monday, 2nd September 2019 | ||||||
| Under 20 Conference A | ||||||
| 02 Sep 2019 Monday 7.30pm | Edinburgh United | 2-1 | Tynecastle | |||
| 02 Sep 2019 Monday 7.45pm | Dalkeith Thistle | 1-1 | Lothian Thistle Hutchison Vale | |||
| 02 Sep 2019 Monday 8.00pm | Upper Annandale | 1-3 | Cumbernauld Colts | |||
| Monday, 2nd September 2019 | ||||||
| Under 20 Conference B | ||||||
| 02 Sep 2019 Monday 7.45pm | Dunipace | 12-2 | Mid Annandale | |||
| 02 Sep 2019 Monday 7.45pm | Musselburgh Athletic | 2-0 | Haddington Athletic | |||
| 02 Sep 2019 Monday 8.00pm | Civil Service Strollers | 3-5 | Preston Athletic | |||
| Tuesday, 3rd September 2019 | ||||||
| Under 20 Conference A | ||||||
| 03 Sep 2019 Tuesday 8.00pm | Dundonald Bluebell | 2-1 | Blackburn United | |||
| Tuesday, 3rd September 2019 | ||||||
| Under 20 Conference B | ||||||
| 03 Sep 2019 Tuesday 7.00pm | Inverkeithing Hillfield Swifts | 0-3 | Penicuik Athletic | |||
| Wednesday, 4th September 2019 | ||||||
| Under 20 Conference B | ||||||
| 04 Sep 2019 Wednesday 7.30pm | Kelty Hearts | 2-2 | Broxburn Athletic | |||
| Friday, 6th September 2019 | ||||||
| Under 20 Conference A | ||||||
| 06 Sep 2019 Friday 7.45pm | Dalkeith Thistle | 0-3 | Edinburgh City | |||
| 06 Sep 2019 Friday 8.00pm | Blackburn United | 1-2 | Edinburgh United | |||
| 06 Sep 2019 Friday 8.00pm | East Fife | 3-3 | Dundonald Bluebell | |||
| 06 Sep 2019 Friday 8.00pm | Edusport Academy | 1-2 | Upper Annandale | |||
| 06 Sep 2019 Friday 8.00pm | Lothian Thistle Hutchison Vale | 3-1 | Hill of Beath Hawthorn | |||
| 06 Sep 2019 Friday 8.00pm | The Spartans | 1-1 | Cumbernauld Colts | |||
| Under 20 Conference B | ||||||
| 06 Sep 2019 Friday 7.45pm | Dunipace | 0-1 | Bonnyton Thistle | |||
| 06 Sep 2019 Friday 7.45pm | Kelty Hearts | 0-3 | Inverkeithing Hillfield Swifts | |||
| 06 Sep 2019 Friday 7.45pm | Musselburgh Athletic | 1-4 | BSC Glasgow | |||
| 06 Sep 2019 Friday 8.00pm | Broxburn Athletic | 0-6 | Camelon Juniors | |||
| 06 Sep 2019 Friday 8.00pm | Mid Annandale | 5-4 | Haddington Athletic | |||
| 06 Sep 2019 Friday 8.00pm | Newtongrange Star | 2-5 | Preston Athletic | |||
| Monday, 9th September 2019 | ||||||
| Under 20 Conference A | ||||||
| 09 Sep 2019 Monday 8.00pm | Edinburgh City | 7-2 | Bonnyrigg Rose | |||
| Tuesday, 10th September 2019 | ||||||
| Under 20 Conference B | ||||||
| 10 Sep 2019 Tuesday 8.00pm | Bonnyton Thistle | 4-4 | BSC Glasgow | |||
| Friday, 13th September 2019 | ||||||
| Under 20 Conference A | ||||||
| 13 Sep 2019 Friday 8.00pm | Dundonald Bluebell | 4-2 | Dalkeith Thistle | |||
| 13 Sep 2019 Friday 8.00pm | Edinburgh United | 5-3 | Bonnyrigg Rose | |||
| 13 Sep 2019 Friday 8.00pm | Hill of Beath Hawthorn | 2-2 | East Fife | |||
| 13 Sep 2019 Friday 8.00pm | Tynecastle | 0-2 | The Spartans | |||
| 13 Sep 2019 Friday 8.00pm | Upper Annandale | 4-6 | Blackburn United | |||
| Under 20 Conference B | ||||||
| 13 Sep 2019 Friday 7.45pm | Musselburgh Athletic | 3-3 | Penicuik Athletic | |||
| 13 Sep 2019 Friday 8.00pm | Bonnyton Thistle | 5-3 | Kelty Hearts | |||
| 13 Sep 2019 Friday 8.00pm | Camelon Juniors | 1-1 | Dunipace | |||
| 13 Sep 2019 Friday 8.00pm | Civil Service Strollers | P-P | BSC Glasgow | |||
| 13 Sep 2019 Friday 8.00pm | Haddington Athletic | 8-0 | Newtongrange Star | |||
| 13 Sep 2019 Friday 8.00pm | Inverkeithing Hillfield Swifts | 5-2 | Mid Annandale | |||
| Monday, 7th October 2019 | ||||||
| Under 20 Conference A | ||||||
| 07 Oct 2019 Monday 7.00pm | Edinburgh University | 0-3 | The Spartans | |||
| Under 20 Conference B | ||||||
| 07 Oct 2019 Monday 8.00pm | Heriot Watt University | 7-0 | Newtongrange Star | |||
| Tuesday, 8th October 2019 | ||||||
| Under 20 Conference A | ||||||
| 08 Oct 2019 Tuesday 8.00pm | Hill of Beath Hawthorn | 2-2 | Caledonian Braves | |||
| Under 20 Conference B | ||||||
| 08 Oct 2019 Tuesday 7.00pm | Camelon Juniors | 2-1 | University of Stirling (SLFL) | |||
| Monday, 14th October 2019 | ||||||
| Under 20 Conference B | ||||||
| 14 Oct 2019 Monday 7.45pm | University of Stirling (SLFL) | 5-0 | Civil Service Strollers | |||
| Tuesday, 15th October 2019 | ||||||
| Under 20 Conference A | ||||||
| 15 Oct 2019 Tuesday 7.30pm | Bonnyrigg Rose | 2-2 | Edinburgh University | |||
| Friday, 18th October 2019 | ||||||
| Under 20 Conference A | ||||||
| 18 Oct 2019 Friday 8.00pm | Caledonian Braves | 0-1 | Blackburn United | |||
| 18 Oct 2019 Friday 8.00pm | Cumbernauld Colts | 0-2 | East Fife | |||
| 18 Oct 2019 Friday 8.00pm | Edinburgh United | 0-5 | Edinburgh City | |||
| 18 Oct 2019 Friday 8.00pm | Edinburgh University | 0-9 | Dundonald Bluebell | |||
| 18 Oct 2019 Friday 8.00pm | Tynecastle | 1-3 | Lothian Thistle Hutchison Vale | |||
| 18 Oct 2019 Friday 8.00pm | Upper Annandale | 2-2 | Dalkeith Thistle | |||
| Under 20 Conference B | ||||||
| 18 Oct 2019 Friday 7.30pm | Newtongrange Star | P-P | Penicuik Athletic | |||
| 18 Oct 2019 Friday 7.45pm | Musselburgh Athletic | 5-2 | Inverkeithing Hillfield Swifts | |||
| 18 Oct 2019 Friday 7.45pm | University of Stirling (SLFL) | 4-2 | BSC Glasgow | |||
| 18 Oct 2019 Friday 8.00pm | Camelon Juniors | 1-3 | Mid Annandale | |||
| 18 Oct 2019 Friday 8.00pm | Civil Service Strollers | 3-2 | Kelty Hearts | |||
| 18 Oct 2019 Friday 8.00pm | Haddington Athletic | 1-1 | Broxburn Athletic | |||
| 18 Oct 2019 Friday 8.00pm | Preston Athletic | 3-2 | Dunipace | |||
| Monday, 21st October 2019 | ||||||
| Under 20 Conference A | ||||||
| 21 Oct 2019 Monday 7.00pm | Edinburgh University | 0-2 | Lothian Thistle Hutchison Vale | |||
| Under 20 Conference B | ||||||
| 21 Oct 2019 Monday 8.00pm | Heriot Watt University | 3-2 | Broxburn Athletic | |||
| 21 Oct 2019 Monday 8.00pm | Preston Athletic | 4-4 | University of Stirling (SLFL) | |||
| Tuesday, 22nd October 2019 | ||||||
| Under 20 Conference A | ||||||
| 22 Oct 2019 Tuesday 8.00pm | Bonnyrigg Rose | 1-3 | The Spartans | |||
| Friday, 25th October 2019 | ||||||
| Under 20 Conference A | ||||||
| 25 Oct 2019 Friday 7.45pm | Dalkeith Thistle | 1-3 | Cumbernauld Colts | |||
| 25 Oct 2019 Friday 8.00pm | Bonnyrigg Rose | 2-0 | Caledonian Braves | |||
| 25 Oct 2019 Friday 8.00pm | Dundonald Bluebell | 4-3 | Edinburgh United | |||
| 25 Oct 2019 Friday 8.00pm | East Fife | P-P | Tynecastle | |||
| 25 Oct 2019 Friday 8.00pm | Hill of Beath Hawthorn | 4-3 | Edinburgh University | |||
| Under 20 Conference B | ||||||
| 25 Oct 2019 Friday 7.45pm | Dunipace | 4-1 | Haddington Athletic | |||
| 25 Oct 2019 Friday 7.45pm | Kelty Hearts | 3-3 | Preston Athletic | |||
| 25 Oct 2019 Friday 8.00pm | Bonnyton Thistle | 3-0 | Musselburgh Athletic | |||
| 25 Oct 2019 Friday 8.00pm | Broxburn Athletic | 1-0 | Newtongrange Star | |||
| 25 Oct 2019 Friday 8.00pm | Camelon Juniors | P-P | Heriot Watt University | |||
| 25 Oct 2019 Friday 8.00pm | Inverkeithing Hillfield Swifts | 1-3 | Civil Service Strollers | |||
| 25 Oct 2019 Friday 8.00pm | Mid Annandale | 4-9 | BSC Glasgow | |||
| 25 Oct 2019 Friday 8.00pm | Penicuik Athletic | 3-1 | University of Stirling (SLFL) | |||
| Monday, 28th October 2019 | ||||||
| Under 20 Conference B | ||||||
| 28 Oct 2019 Monday 7.45pm | University of Stirling (SLFL) | 1-4 | Heriot Watt University | |||
| Friday, 8th November 2019 | ||||||
| Under 20 Knock Out Cup (1st Round) | ||||||
| 08 Nov 2019 Friday 7.45pm | Musselburgh Athletic | 2-3 | Blackburn United | |||
| 08 Nov 2019 Friday 8.00pm | BSC Glasgow | 4-5 | Camelon Juniors | |||
| 08 Nov 2019 Friday 8.00pm | Civil Service Strollers | 3-1 | Hill of Beath Hawthorn | |||
| 08 Nov 2019 Friday 8.00pm | Cumbernauld Colts | 2-1 | Broxburn Athletic | |||
| 08 Nov 2019 Friday 8.00pm | Dalkeith Thistle | 0-1 | Caledonian Braves | |||
| 08 Nov 2019 Friday 8.00pm | Edinburgh City | 4-2 | Lothian Thistle Hutchison Vale | |||
| 08 Nov 2019 Friday 8.00pm | Haddington Athletic | 2-7 | Edinburgh United | |||
| 08 Nov 2019 Friday 8.00pm | Heriot Watt University | 2-1 | Mid Annandale | |||
| 08 Nov 2019 Friday 8.00pm | Inverkeithing Hillfield Swifts | 2-3 | Bonnyton Thistle | |||
| 08 Nov 2019 Friday 8.00pm | Newtongrange Star | 0-7 | Dundonald Bluebell | |||
| 08 Nov 2019 Friday 8.00pm | Penicuik Athletic | 2-4 | University of Stirling (SLFL) | |||
| 08 Nov 2019 Friday 8.00pm | Upper Annandale | 4-1 | East Fife | |||
| Scottish FA Youth Cup (2nd Round) | ||||||
| 08 Nov 2019 Friday 7.00pm | Dunipace | 1-3 aet | Ross County | |||
| 08 Nov 2019 Friday 7.30pm | Kelty Hearts | 0-1 | Bonnyrigg Rose | |||
| Friday, 15th November 2019 | ||||||
| Under 20 Conference A | ||||||
| 15 Nov 2019 Friday 8.00pm | Blackburn United | 0-2 | Dalkeith Thistle | |||
| 15 Nov 2019 Friday 8.00pm | Cumbernauld Colts | 1-4 | Edinburgh City | |||
| 15 Nov 2019 Friday 8.00pm | Edinburgh United | 4-0 | Hill of Beath Hawthorn | |||
| 15 Nov 2019 Friday 8.00pm | Upper Annandale | 5-2 | Dundonald Bluebell | |||
| 15 Nov 2019 Friday 8.15pm | The Spartans | 2-0 | East Fife | |||
| Under 20 Conference B | ||||||
| 15 Nov 2019 Friday 7.30pm | Newtongrange Star | 1-2 | Heriot Watt University | |||
| 15 Nov 2019 Friday 7.45pm | Musselburgh Athletic | 3-4 | Camelon Juniors | |||
| 15 Nov 2019 Friday 7.45pm | University of Stirling (SLFL) | 8-0 | Broxburn Athletic | |||
| 15 Nov 2019 Friday 8.00pm | BSC Glasgow | 6-3 | Penicuik Athletic | |||
| 15 Nov 2019 Friday 8.00pm | Civil Service Strollers | P-P | Bonnyton Thistle | |||
| 15 Nov 2019 Friday 8.00pm | Preston Athletic | 0-2 | Inverkeithing Hillfield Swifts | |||
| Under 20 Knock Out Cup (1st Round) | ||||||
| 15 Nov 2019 Friday 8.00pm | Bonnyrigg Rose | 5-3 | Edinburgh University | |||
| 15 Nov 2019 Friday 8.00pm | Tynecastle | AW | Dunipace | |||
| Friday, 22nd November 2019 | ||||||
| Under 20 Conference A | ||||||
| 22 Nov 2019 Friday 7.45pm | Dalkeith Thistle | 1-0 | The Spartans | |||
| 22 Nov 2019 Friday 8.00pm | Bonnyrigg Rose | 1-0 | Cumbernauld Colts | |||
| 22 Nov 2019 Friday 8.00pm | Caledonian Braves | 2-1 | East Fife | |||
| 22 Nov 2019 Friday 8.00pm | Edinburgh University | 2-1 | Edinburgh United | |||
| 22 Nov 2019 Friday 8.00pm | Hill of Beath Hawthorn | 0-4 | Upper Annandale | |||
| 22 Nov 2019 Friday 8.00pm | Lothian Thistle Hutchison Vale | 3-1 | Blackburn United | |||
| Under 20 Conference B | ||||||
| 22 Nov 2019 Friday 7.45pm | Dunipace | 1-11 | University of Stirling (SLFL) | |||
| 22 Nov 2019 Friday 8.00pm | Bonnyton Thistle | 4-3 | Preston Athletic | |||
| 22 Nov 2019 Friday 8.00pm | Broxburn Athletic | 0-9 | BSC Glasgow | |||
| 22 Nov 2019 Friday 8.00pm | Heriot Watt University | 0-1 | Musselburgh Athletic | |||
| 22 Nov 2019 Friday 8.00pm | Mid Annandale | 2-2 | Penicuik Athletic | |||
| Under 20 Challenge Cup (1st Round) | ||||||
| 22 Nov 2019 Friday 7.45pm | Kelty Hearts | 6-0 | Camelon Juniors | |||
| 22 Nov 2019 Friday 8.00pm | Dundonald Bluebell | 1-2 | Civil Service Strollers | |||
| Friday, 29th November 2019 | ||||||
| Under 20 Conference A | ||||||
| 29 Nov 2019 Friday 8.00pm | Blackburn United | 3-2 | East Fife | |||
| 29 Nov 2019 Friday 8.00pm | Bonnyrigg Rose | 1-0 | Lothian Thistle Hutchison Vale | |||
| 29 Nov 2019 Friday 8.00pm | Caledonian Braves | A-A | Dalkeith Thistle | |||
| 29 Nov 2019 Friday 8.00pm | Cumbernauld Colts | 5-0 | Hill of Beath Hawthorn | |||
| 29 Nov 2019 Friday 8.00pm | Edinburgh United | P-P | Dundonald Bluebell | |||
| 29 Nov 2019 Friday 8.00pm | The Spartans | 2-3 | Edinburgh City | |||
| 29 Nov 2019 Friday 8.00pm | Upper Annandale | 0-4 | Edinburgh University | |||
| Under 20 Conference B | ||||||
| 29 Nov 2019 Friday 7.30pm | Newtongrange Star | P-P | Inverkeithing Hillfield Swifts | |||
| 29 Nov 2019 Friday 7.45pm | Musselburgh Athletic | 1-1 | Mid Annandale | |||
| 29 Nov 2019 Friday 7.45pm | University of Stirling (SLFL) | P-P | Kelty Hearts | |||
| 29 Nov 2019 Friday 8.00pm | BSC Glasgow | 1-1 | Dunipace | |||
| 29 Nov 2019 Friday 8.00pm | Civil Service Strollers | 0-2 | Heriot Watt University | |||
| 29 Nov 2019 Friday 8.00pm | Penicuik Athletic | 1-0 | Broxburn Athletic | |||
| 29 Nov 2019 Friday 8.00pm | Preston Athletic | 5-1 | Camelon Juniors | |||
| Tuesday, 3rd December 2019 | ||||||
| Under 20 Knock Out Cup (1st Round) | ||||||
| 03 Dec 2019 Tuesday 7.30pm | Preston Athletic | 1-6 | The Spartans | |||
| Monday, 9th December 2019 | ||||||
| Under 20 Conference B | ||||||
| 09 Dec 2019 Monday 8.00pm | Civil Service Strollers | 2-2 | Bonnyton Thistle | |||
| Friday, 13th December 2019 | ||||||
| Under 20 Conference A | ||||||
| 13 Dec 2019 Friday 8.00pm | Blackburn United | 0-5 | Edinburgh City | |||
| 13 Dec 2019 Friday 8.00pm | Bonnyrigg Rose | 1-1 | Dalkeith Thistle | |||
| 13 Dec 2019 Friday 8.00pm | Caledonian Braves | 2-1 | Dundonald Bluebell | |||
| 13 Dec 2019 Friday 8.00pm | Cumbernauld Colts | 0-3 | Edinburgh United | |||
| 13 Dec 2019 Friday 8.00pm | Edinburgh University | P-P | Upper Annandale | |||
| 13 Dec 2019 Friday 8.00pm | Lothian Thistle Hutchison Vale | 1-2 | East Fife | |||
| 13 Dec 2019 Friday 8.00pm | The Spartans | 2-1 | Hill of Beath Hawthorn | |||
| Under 20 Conference B | ||||||
| 13 Dec 2019 Friday 7.45pm | University of Stirling (SLFL) | P-P | Bonnyton Thistle | |||
| 13 Dec 2019 Friday 8.00pm | Broxburn Athletic | 1-1 | Dunipace | |||
| 13 Dec 2019 Friday 8.00pm | BSC Glasgow | 6-2 | Inverkeithing Hillfield Swifts | |||
| 13 Dec 2019 Friday 8.00pm | Camelon Juniors | 6-0 | Newtongrange Star | |||
| 13 Dec 2019 Friday 8.00pm | Civil Service Strollers | 4-4 | Mid Annandale | |||
| 13 Dec 2019 Friday 8.00pm | Penicuik Athletic | 4-5 | Kelty Hearts | |||
| 13 Dec 2019 Friday 8.00pm | Preston Athletic | 1-3 | Musselburgh Athletic | |||
| Wednesday, 18th December 2019 | ||||||
| Under 20 Challenge Cup (2nd Round) | ||||||
| 18 Dec 2019 Wednesday 8.00pm | Preston Athletic | 1-1 (3-2 pens) | Dalkeith Thistle | |||
| Friday, 20th December 2019 | ||||||
| Under 20 Conference A | ||||||
| 20 Dec 2019 Friday 8.00pm | Cumbernauld Colts | 1-3 | Upper Annandale | |||
| Under 20 Conference B | ||||||
| 20 Dec 2019 Friday 8.00pm | BSC Glasgow | 5-0 | Newtongrange Star | |||
| 20 Dec 2019 Friday 8.00pm | Inverkeithing Hillfield Swifts | P-P | Camelon Juniors | |||
| Under 20 Challenge Cup (2nd Round) | ||||||
| 20 Dec 2019 Friday 7.45pm | Kelty Hearts | 3-2 | Caledonian Braves | |||
| 20 Dec 2019 Friday 8.00pm | Blackburn United | 10-0 | Broxburn Athletic | |||
| 20 Dec 2019 Friday 8.00pm | Bonnyton Thistle | 1-5 | University of Stirling (SLFL) | |||
| 20 Dec 2019 Friday 8.00pm | Dunipace | 3-2 | Heriot Watt University | |||
| 20 Dec 2019 Friday 8.00pm | East Fife | 2-1 | Bonnyrigg Rose | |||
| 20 Dec 2019 Friday 8.00pm | The Spartans | 0-4 | Lothian Thistle Hutchison Vale | |||
| 20 Dec 2019 Friday 8.15pm | Edinburgh City | 5-1 | Civil Service Strollers | |||
| Friday, 10th January 2020 | ||||||
| Under 20 Conference A | ||||||
| 10 Jan 2020 Friday 8.00pm | East Fife | 3-0 | Hill of Beath Hawthorn | |||
| 10 Jan 2020 Friday 8.00pm | Lothian Thistle Hutchison Vale | 8-0 | Edinburgh University | |||
| Under 20 Conference B | ||||||
| 10 Jan 2020 Friday 7.30pm | Newtongrange Star | 3-4 | Inverkeithing Hillfield Swifts | |||
| 10 Jan 2020 Friday 8.00pm | Mid Annandale | 0-6 | Musselburgh Athletic | |||
| 10 Jan 2020 Friday 8.00pm | Preston Athletic | 4-1 | BSC Glasgow | |||
| Under 20 Knock Out Cup (2nd Round) | ||||||
| 10 Jan 2020 Friday 8.00pm | Bonnyton Thistle | 3-2 | Blackburn United | |||
| 10 Jan 2020 Friday 8.00pm | Camelon Juniors | 1-7 | Edinburgh United | |||
| 10 Jan 2020 Friday 8.00pm | Civil Service Strollers | 3-2 | Dundonald Bluebell | |||
| 10 Jan 2020 Friday 8.00pm | Dunipace | 2-3 | Caledonian Braves | |||
| 10 Jan 2020 Friday 8.00pm | Heriot Watt University | 2-0 | Kelty Hearts | |||
| 10 Jan 2020 Friday 8.00pm | The Spartans | 4-0 | Cumbernauld Colts | |||
| 10 Jan 2020 Friday 8.00pm | Upper Annandale | 3-7 | University of Stirling (SLFL) | |||
| 10 Jan 2020 Friday 8.15pm | Edinburgh City | 5-1 | Bonnyrigg Rose | |||
| Under 20 League Cup | ||||||
| 10 Jan 2020 Friday 8.00pm | Penicuik Athletic | 9-0 | Dalkeith Thistle | |||
| Friday, 17th January 2020 | ||||||
| Under 20 Conference A | ||||||
| 17 Jan 2020 Friday 7.45pm | Dalkeith Thistle | 1-1 | East Fife | |||
| 17 Jan 2020 Friday 8.00pm | Dundonald Bluebell | 5-4 | Bonnyrigg Rose | |||
| 17 Jan 2020 Friday 8.00pm | Edinburgh City | 1-2 | Lothian Thistle Hutchison Vale | |||
| 17 Jan 2020 Friday 8.00pm | Edinburgh United | 5-2 | The Spartans | |||
| 17 Jan 2020 Friday 8.00pm | Edinburgh University | 0-1 | Caledonian Braves | |||
| 17 Jan 2020 Friday 8.00pm | Hill of Beath Hawthorn | 0-1 | Blackburn United | |||
| Under 20 Conference B | ||||||
| 17 Jan 2020 Friday 7.45pm | Kelty Hearts | 2-1 | Dunipace | |||
| 17 Jan 2020 Friday 7.45pm | Musselburgh Athletic | 3-1 | Newtongrange Star | |||
| 17 Jan 2020 Friday 8.00pm | Bonnyton Thistle | 0-3 | Penicuik Athletic | |||
| 17 Jan 2020 Friday 8.00pm | BSC Glasgow | 8-1 | Camelon Juniors | |||
| 17 Jan 2020 Friday 8.00pm | Inverkeithing Hillfield Swifts | 1-2 | Broxburn Athletic | |||
| 17 Jan 2020 Friday 8.00pm | Preston Athletic | 2-3 | Mid Annandale | |||
| 17 Jan 2020 Friday 8.15pm | Heriot Watt University | 3-3 | University of Stirling (SLFL) | |||
| Friday, 24th January 2020 | ||||||
| Under 20 Conference A | ||||||
| 24 Jan 2020 Friday 8.00pm | Blackburn United | 3-2 | Edinburgh University | |||
| 24 Jan 2020 Friday 8.00pm | Caledonian Braves | 1-2 | Edinburgh United | |||
| 24 Jan 2020 Friday 8.00pm | East Fife | 1-5 | Edinburgh City | |||
| 24 Jan 2020 Friday 8.00pm | Hill of Beath Hawthorn | 1-1 | Cumbernauld Colts | |||
| 24 Jan 2020 Friday 8.00pm | Lothian Thistle Hutchison Vale | 6-3 | Dundonald Bluebell | |||
| 24 Jan 2020 Friday 8.00pm | The Spartans | 6-1 | Upper Annandale | |||
| Under 20 Conference B | ||||||
| 24 Jan 2020 Friday 7.45pm | Dunipace | 3-0 | Inverkeithing Hillfield Swifts | |||
| 24 Jan 2020 Friday 7.45pm | University of Stirling (SLFL) | 3-0 | Musselburgh Athletic | |||
| 24 Jan 2020 Friday 8.00pm | Broxburn Athletic | 0-3 | Bonnyton Thistle | |||
| 24 Jan 2020 Friday 8.00pm | BSC Glasgow | 4-4 | Heriot Watt University | |||
| 24 Jan 2020 Friday 8.00pm | Mid Annandale | 1-3 | Kelty Hearts | |||
| 24 Jan 2020 Friday 8.00pm | Newtongrange Star | 0-5 | Civil Service Strollers | |||
| 24 Jan 2020 Friday 8.00pm | Penicuik Athletic | 3-0 | Camelon Juniors | |||
| Sunday, 26th January 2020 | ||||||
| Scottish FA Youth Cup | ||||||
| 26 Jan 2020 Sunday 2:30pm | Kilmarnock | 6-0 | Bonnyrigg Rose | |||
| Friday, 31st January 2020 | ||||||
| Under 20 Conference A | ||||||
| 31 Jan 2020 Friday 8.00pm | Cumbernauld Colts | 0-4 | The Spartans | |||
| 31 Jan 2020 Friday 8.00pm | Dundonald Bluebell | 1-0 | East Fife | |||
| 31 Jan 2020 Friday 8.00pm | Edinburgh City | 3-0 | Dalkeith Thistle | |||
| 31 Jan 2020 Friday 8.00pm | Edinburgh United | 2-0 | Blackburn United | |||
| 31 Jan 2020 Friday 8.00pm | Edinburgh University | 2-7 | Bonnyrigg Rose | |||
| 31 Jan 2020 Friday 8.00pm | Upper Annandale | 0-5 | Caledonian Braves | |||
| Under 20 Conference B | ||||||
| 31 Jan 2020 Friday 8.00pm | Bonnyton Thistle | 1-4 | Dunipace | |||
| 31 Jan 2020 Friday 8.00pm | BSC Glasgow | 5-2 | Musselburgh Athletic | |||
| 31 Jan 2020 Friday 8.00pm | Camelon Juniors | 2-1 | Broxburn Athletic | |||
| 31 Jan 2020 Friday 8.00pm | Civil Service Strollers | 0-2 | University of Stirling (SLFL) | |||
| 31 Jan 2020 Friday 8.00pm | Heriot Watt University | 3-2 | Penicuik Athletic | |||
| 31 Jan 2020 Friday 8.00pm | Inverkeithing Hillfield Swifts | 5-1 | Kelty Hearts | |||
| 31 Jan 2020 Friday 8.00pm | Preston Athletic | 8-1 | Newtongrange Star | |||
| Friday, 7th February 2020 | ||||||
| Under 20 Conference A | ||||||
| 07 Feb 2020 Friday 8.00pm | Caledonian Braves | 1-4 | Cumbernauld Colts | |||
| Under 20 Conference B | ||||||
| 07 Feb 2020 Friday 7.45pm | Dunipace | 3-2 | BSC Glasgow | |||
| Friday, 7th February 2020 | ||||||
| Under 20 Conference B | ||||||
| 07 Feb 2020 Friday 7.45pm | Kelty Hearts | 1-1 | Bonnyton Thistle | |||
| 07 Feb 2020 Friday 8.00pm | Broxburn Athletic | 0-2 | Heriot Watt University | |||
| 07 Feb 2020 Friday 8.00pm | Penicuik Athletic | 4-4 | Musselburgh Athletic | |||
| Under 20 League Cup (2nd Round) | ||||||
| 07 Feb 2020 Friday 8.00pm | Camelon Juniors | 4-1 | East Fife | |||
| 07 Feb 2020 Friday 8.00pm | Dundonald Bluebell | 0-1 | University of Stirling (SLFL) | |||
| 07 Feb 2020 Friday 8.00pm | Edinburgh City | 2-0 | Edinburgh United | |||
| 07 Feb 2020 Friday 8.00pm | Hill of Beath Hawthorn | 0-4 | Civil Service Strollers | |||
| 07 Feb 2020 Friday 8.00pm | Preston Athletic | 1-3 | Bonnyrigg Rose | |||
| 07 Feb 2020 Friday 8.00pm | Upper Annandale | 1-7 | Lothian Thistle Hutchison Vale | |||
| Friday, 14th February 2020 | ||||||
| Under 20 Conference A | ||||||
| 14 Feb 2020 Friday 8.00pm | Caledonian Braves | 1-5 | The Spartans | |||
| 14 Feb 2020 Friday 8.00pm | Cumbernauld Colts | 2-3 | Blackburn United | |||
| 14 Feb 2020 Friday 8.00pm | Dundonald Bluebell | 0-2 | Edinburgh City | |||
| 14 Feb 2020 Friday 8.00pm | Edinburgh United | 0-3 | Lothian Thistle Hutchison Vale | |||
| 14 Feb 2020 Friday 8.00pm | Edinburgh University | 1-8 | East Fife | |||
| 14 Feb 2020 Friday 8.00pm | Hill of Beath Hawthorn | 4-2 | Dalkeith Thistle | |||
| 14 Feb 2020 Friday 8.00pm | Upper Annandale | 1-5 | Bonnyrigg Rose | |||
| Under 20 Conference B | ||||||
| 14 Feb 2020 Friday 7.45pm | Dunipace | 1-0 | Heriot Watt University | |||
| 14 Feb 2020 Friday 7.45pm | Musselburgh Athletic | 3-0 | Broxburn Athletic | |||
| 14 Feb 2020 Friday 7.45pm | University of Stirling (SLFL) | 9-1 | Preston Athletic | |||
| 14 Feb 2020 Friday 8.00pm | Bonnyton Thistle | 2-3 | Inverkeithing Hillfield Swifts | |||
| 14 Feb 2020 Friday 8.00pm | Camelon Juniors | 1-2 | Kelty Hearts | |||
| 14 Feb 2020 Friday 8.00pm | Civil Service Strollers | 1-2 | Penicuik Athletic | |||
| 14 Feb 2020 Friday 8.00pm | Newtongrange Star | P-P | Mid Annandale | |||
| Friday, 28th February 2020 | ||||||
| Under 20 Conference A | ||||||
| 28 Feb 2020 Friday 7.45pm | Dalkeith Thistle | 1-5 | Edinburgh University | |||
| 28 Feb 2020 Friday 8.00pm | Blackburn United | A-A | Bonnyrigg Rose | |||
| 28 Feb 2020 Friday 8.00pm | Dundonald Bluebell | P-P | Cumbernauld Colts | |||
| 28 Feb 2020 Friday 8.00pm | East Fife | 5-0 | Edinburgh United | |||
| 28 Feb 2020 Friday 8.00pm | Lothian Thistle Hutchison Vale | 4-3 | Upper Annandale | |||
| 28 Feb 2020 Friday 8.15pm | Edinburgh City | 7-2 | Hill of Beath Hawthorn | |||
| Under 20 Conference B | ||||||
| 28 Feb 2020 Friday 7.45pm | Dunipace | P-P | Musselburgh Athletic | |||
| 28 Feb 2020 Friday 7.45pm | University of Stirling (SLFL) | 11-0 | Newtongrange Star | |||
| 28 Feb 2020 Friday 8.00pm | Broxburn Athletic | 1-2 | Civil Service Strollers | |||
| 28 Feb 2020 Friday 8.00pm | Heriot Watt University | 1-1 | Kelty Hearts | |||
| 28 Feb 2020 Friday 8.00pm | Inverkeithing Hillfield Swifts | 5-4 | Camelon Juniors | |||
| 28 Feb 2020 Friday 8.00pm | Mid Annandale | 0-3 | Bonnyton Thistle | |||
| 28 Feb 2020 Friday 8.00pm | Penicuik Athletic | P-P | Preston Athletic | |||
| Friday, 6th March 2020 | ||||||
| Under 20 Conference A | ||||||
| 06 Mar 2020 Friday 8.00pm | Caledonian Braves | 2-1 | Bonnyrigg Rose | |||
| 06 Mar 2020 Friday 8.00pm | Cumbernauld Colts | 0-6 | Lothian Thistle Hutchison Vale | |||
| 06 Mar 2020 Friday 8.00pm | Edinburgh United | 1-2 | Dalkeith Thistle | |||
| 06 Mar 2020 Friday 8.00pm | Edinburgh University | 0-11 | Edinburgh City | |||
| 06 Mar 2020 Friday 8.00pm | Hill of Beath Hawthorn | P-P | Dundonald Bluebell | |||
| 06 Mar 2020 Friday 8.00pm | The Spartans | 5-1 | Blackburn United | |||
| 06 Mar 2020 Friday 8.00pm | Upper Annandale | 1-3 | East Fife | |||
| Under 20 Conference B | ||||||
| 06 Mar 2020 Friday 7.45pm | Musselburgh Athletic | 4-0 | Kelty Hearts | |||
| 06 Mar 2020 Friday 7.45pm | University of Stirling (SLFL) | 14-0 | Mid Annandale | |||
| 06 Mar 2020 Friday 8.00pm | Camelon Juniors | 4-2 | Bonnyton Thistle | |||
| 06 Mar 2020 Friday 8.00pm | Inverkeithing Hillfield Swifts | 2-3 | Heriot Watt University | |||
| 06 Mar 2020 Friday 8.00pm | Newtongrange Star | 0-1 | BSC Glasgow | |||
| 06 Mar 2020 Friday 8.00pm | Penicuik Athletic | 1-0 | Civil Service Strollers | |||
| 06 Mar 2020 Friday 8.00pm | Preston Athletic | P-P | Broxburn Athletic | |||
