| 2019-07-06 15:00:24July 6, 2019 | Vale of Leithen | 3 - 3 | Edinburgh Star | Friendly | 2019/20 | Victoria Park | Recap |
| 2019-07-09 19:30:17July 9, 2019 | Vale of Leithen | 1 - 2 | Penicuik Athletic | Friendly | 2019/20 | Victoria Park | Recap |
| 2019-07-13 13:00:25July 13, 2019 | Dunbar United | 1 - 1 | Vale of Leithen | Friendly | 2019/20 | New Countess Park | Recap |
| 2019-07-17 19:30:51July 17, 2019 | Vale of Leithen | 5 - 2 | Hawick Royal Albert | Friendly | 2019/20 | Victoria Park | Recap |
| 2019-07-20 14:30:37July 20, 2019 | Dalkieth Thistle | 1 - 4 | Vale of Leithen | Friendly | 2019/20 | King's Park Croft Street Dalkeith | Recap |
| 2019-07-23 19:30:29July 23, 2019 | Vale of Leithen | 1 - 1 | Upper Annandale | Friendly | 2019/20 | Victoria Park | Recap |
| 2019-07-27 15:00:42July 27, 2019 | Bonnyrigg Rose | 6 - 0 | Vale of Leithen | Lowland League | 2019/20 | New Dundas Park | Recap |
| 2019-07-30 19:15:46July 30, 2019 | Vale of Leithen | 1 - 5 | Gala Fairydean Rovers | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-08-03 15:00:34August 3, 2019 | Vale of Leithen | 0 - 3 | East Kilbride | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-08-10 15:00:05August 10, 2019 | Edinburgh University | 3 - 1 | Vale of Leithen | Lowland League | 2019/20 | Peffermill | Recap |
| 2019-08-17 15:00:01August 17, 2019 | Edinburgh University | 1 - 0 | Vale of Leithen | Football Nation EOS Qualifying Cup | 2019/20 | Peffermill | Recap |
| 2019-08-24 15:00:32August 24, 2019 | Vale of Leithen | 0 - 7 | Kelty Hearts | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-08-28 19:45:40August 28, 2019 | Stirling University | 4 - 0 | Vale of Leithen | Lowland League | 2019/20 | Forthbank | Recap |
| 2019-08-31 15:00:54August 31, 2019 | BSC Glasgow | 3 - 0 | Vale of Leithen | Lowland League | 2019/20 | Indodrill Park (Alloa) | Recap |
| 2019-09-07 15:00:00September 7, 2019 | Vale of Leithen | 0 - 3 | Caledonian Braves | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-09-14 15:00:11September 14, 2019 | Vale of Leithen | 1 - 6 | Kelty Hearts | South Challenge Cup | 2019/20 | Victoria Park | Recap |
| 2019-09-21 15:00:42September 21, 2019 | Fort William | 5 - 0 | Vale of Leithen | William Hill Scottish Cup | 2019/20 | Claggan Park | Recap |
| 2019-09-28 15:00:35September 28, 2019 | Dalbeattie Star | 1 - 3 | Vale of Leithen | Lowland League | 2019/20 | Islecroft Stadium | Recap |
| 2019-10-02 19:45:01October 2, 2019 | East Stirlingshire | 6 - 1 | Vale of Leithen | Lowland League | 2019/20 | Falkirk Stadium | Recap |
| 2019-10-05 15:00:38October 5, 2019 | Vale of Leithen | 2 - 2 | Cumbernauld Colts | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-10-26 15:00:09October 26, 2019 | Gretna 2008 | 2 - 0 | Vale of Leithen | Lowland League | 2019/20 | Raydale | Recap |
| 2019-11-02 14:00:55November 2, 2019 | Vale of Leithen | 2 - 4 | Civil Service Strollers | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-11-16 15:00:39November 16, 2019 | Berwick Rangers | 4 - 0 | Vale of Leithen | Lowland League | 2019/20 | Shielfield Park | Recap |
| 2019-11-23 14:00:53November 23, 2019 | Vale of Leithen | 1 - 5 | Spartans | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-12-07 14:00:23December 7, 2019 | Vale of Leithen | 0 - 2 | Bonnyrigg Rose | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-12-14 15:00:46December 14, 2019 | Kelty Hearts | 11 - 0 | Vale of Leithen | Lowland League | 2019/20 | New Central Park | Recap |
| 2019-12-21 14:00:38December 21, 2019 | Vale of Leithen | 1 - 1 | Edinburgh University | Lowland League | 2019/20 | Victoria Park | Recap |
| 2019-12-28 15:00:09December 28, 2019 | Gala Fairydean Rovers | 1 - 3 | Vale of Leithen | Lowland League | 2019/20 | Netherdale | Recap |
| 2020-01-04 15:00:02January 4, 2020 | Caledonian Braves | 4 - 1 | Vale of Leithen | Lowland League | 2019/20 | Alliance Park | Recap |
| 2020-01-11 14:00:13January 11, 2020 | Vale of Leithen | P - P | Berwick Rangers | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-01-25 14:00:25January 25, 2020 | Vale of Leithen | 0 - 3 | East Stirlingshire | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-02-01 15:00:00February 1, 2020 | Cumbernauld Colts | 7 - 1 | Vale of Leithen | Lowland League | 2019/20 | Broadwood | Recap |
| 2020-02-08 14:00:40February 8, 2020 | Vale of Leithen | P - P | BSC Glasgow | Lowland League | 2019/20 | Pennypit | Recap |
| 2020-02-15 15:00:05February 15, 2020 | Vale of Leithen | P - P | Gretna 2008 | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-02-22 15:00:09February 22, 2020 | Vale of Leithen | P - P | Dalbeattie Star | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-02-28 19:45:57February 28, 2020 | Spartans | 2 - 1 | Vale of Leithen | Lowland League | 2019/20 | Ainslie Park | Recap |
| 2020-03-07 15:00:04March 7, 2020 | Vale of Leithen | P - P | Dalbeattie Star | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-03-14 15:00:41March 14, 2020 | Vale of Leithen | P - P | Berwick Rangers | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-03-21 15:00:57March 21, 2020 | East Kilbride | P - P | Vale of Leithen | Lowland League | 2019/20 | K Park | Recap |
| 2020-03-28 15:00:57March 28, 2020 | Vale of Leithen | P - P | BSC Glasgow | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-04-04 15:00:01April 4, 2020 | Vale of Leithen | P - P | Gretna 2008 | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-04-08 19:45:37April 8, 2020 | Vale of Leithen | P - P | Dalbeattie Star | Lowland League | 2019/20 | Victoria Park | Recap |
| 2020-04-11 15:00:47April 11, 2020 | Civil Service Strollers | P - P | Vale of Leithen | Lowland League | 2019/20 | Marine Drive | Preview |
| 2020-04-18 15:00:29April 18, 2020 | Vale of Leithen | P - P | Stirling University | Lowland League | 2019/20 | Victoria Park | Preview |
