| 2018-07-14 13:00:12July 14, 2018 | Edinburgh United | 0 - 2 | Vale of Leithen | | 2018/19 | Meggatland Astro | Recap |
| 2018-07-17 19:30:09July 17, 2018 | Easthouses Lily | 2 - 2 | Vale of Leithen | | 2018/19 | Newbattle Complex | Recap |
| 2018-07-21 14:00:13July 21, 2018 | Newburgh Juniors | 4 - 8 | Vale of Leithen | | 2018/19 | East Shore Park, Newburgh | Recap |
| 2018-07-24 20:00:39July 24, 2018 | Tollcross Thistle | 3 - 2 | Vale of Leithen | | 2018/19 | Peffermill | Recap |
| 2018-07-28 15:00:47July 28, 2018 | Civil Service Strollers | 0 - 0 | Vale of Leithen | Lowland League | 2018/19 | Marine Drive | Recap |
| 2018-07-31 19:15:46July 31, 2018 | Vale of Leithen | 4 - 2 | Gala Fairydean Rovers | Lowland League | 2018/19 | Victoria Park | Recap |
| 2018-08-04 15:00:53August 4, 2018 | Vale of Leithen | 1 - 4 | Spartans | Lowland League | 2018/19 | Victoria Park | Recap |
| 2018-08-10 19:00:52August 10, 2018 | Vale of Leithen | 2 - 4 | Celtic XI | | 2018/19 | Victoria Park | Recap |
| 2018-08-11 15:00:57August 11, 2018 | East Kilbride | 5 - 1 | Vale of Leithen | Lowland League | 2018/19 | K Park | Recap |
| 2018-08-18 14:30:08August 18, 2018 | Oakley United | 14:30:082:30 pm | Vale of Leithen | Football Nation EOS Qualifying Cup | 2018/19 | Blairwood Park | Preview |
| 2018-08-25 15:00:05August 25, 2018 | Vale of Leithen | 15:00:053:00 pm | Gretna 2008 | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-08-29 19:45:01August 29, 2018 | East Stirlingshire | 19:45:017:45 pm | Vale of Leithen | Lowland League | 2018/19 | Falkirk Stadium | Preview |
| 2018-09-01 15:00:32September 1, 2018 | Vale of Leithen | 15:00:323:00 pm | Kelty Hearts | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-09-08 15:00:22September 8, 2018 | Edusport Academy | 15:00:223:00 pm | Vale of Leithen | Lowland League | 2018/19 | Galabank | Preview |
| 2018-09-15 15:00:01September 15, 2018 | Vale of Leithen | 15:00:013:00 pm | Jeanfield Swifts | South Challenge Cup | 2018/19 | Victoria Park | Preview |
| 2018-09-29 15:00:40September 29, 2018 | Stirling University | 15:00:403:00 pm | Vale of Leithen | Lowland League | 2018/19 | Forthbank | Preview |
| 2018-10-02 19:45:05October 2, 2018 | Edinburgh University | 19:45:057:45 pm | Vale of Leithen | Lowland League | 2018/19 | Peffermill | Preview |
| 2018-10-06 15:00:09October 6, 2018 | Vale of Leithen | 15:00:093:00 pm | Dalbeattie Star | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-10-26 19:45:54October 26, 2018 | BSC Glasgow | 19:45:547:45 pm | Vale of Leithen | Lowland League | 2018/19 | Recreation Park (Alloa) | Preview |
| 2018-11-03 14:00:23November 3, 2018 | Vale of Leithen | 14:00:232:00 pm | Whitehill Welfare | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-11-17 14:00:37November 17, 2018 | Vale of Leithen | 14:00:372:00 pm | Selkirk | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-11-24 14:00:38November 24, 2018 | Vale of Leithen | 14:00:382:00 pm | Cumbernauld Colts | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-12-08 15:00:57December 8, 2018 | Spartans | 15:00:573:00 pm | Vale of Leithen | Lowland League | 2018/19 | Ainslie Park | Preview |
| 2018-12-15 14:00:25December 15, 2018 | Vale of Leithen | 14:00:252:00 pm | East Stirlingshire | Lowland League | 2018/19 | Victoria Park | Preview |
| 2018-12-22 15:00:46December 22, 2018 | Kelty Hearts | 15:00:463:00 pm | Vale of Leithen | Lowland League | 2018/19 | New Central Park | Preview |
| 2018-12-29 15:00:09December 29, 2018 | Gala Fairydean Rovers | 15:00:093:00 pm | Vale of Leithen | Lowland League | 2018/19 | Netherdale | Preview |
| 2019-01-05 14:00:00January 5, 2019 | Vale of Leithen | 14:00:002:00 pm | Edusport Academy | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-01-12 14:00:43January 12, 2019 | Selkirk | 14:00:432:00 pm | Vale of Leithen | Lowland League | 2018/19 | Yarrow Park | Preview |
| 2019-01-26 14:00:55January 26, 2019 | Vale of Leithen | 14:00:552:00 pm | Civil Service Strollers | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-02-02 15:00:00February 2, 2019 | Cumbernauld Colts | 15:00:003:00 pm | Vale of Leithen | Lowland League | 2018/19 | Broadwood | Preview |
| 2019-02-09 15:00:34February 9, 2019 | Vale of Leithen | 15:00:343:00 pm | East Kilbride | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-02-16 15:00:42February 16, 2019 | Whitehill Welfare | 15:00:423:00 pm | Vale of Leithen | Lowland League | 2018/19 | Ferguson Park | Preview |
| 2019-02-23 15:00:29February 23, 2019 | Vale of Leithen | 15:00:293:00 pm | Stirling University | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-03-09 15:00:40March 9, 2019 | Vale of Leithen | 15:00:403:00 pm | BSC Glasgow | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-03-16 15:00:09March 16, 2019 | Gretna 2008 | 15:00:093:00 pm | Vale of Leithen | Lowland League | 2018/19 | Raydale | Preview |
| 2019-04-13 15:00:38April 13, 2019 | Vale of Leithen | 15:00:383:00 pm | Edinburgh University | Lowland League | 2018/19 | Victoria Park | Preview |
| 2019-04-20 15:00:35April 20, 2019 | Dalbeattie Star | 15:00:353:00 pm | Vale of Leithen | Lowland League | 2018/19 | Islecroft Stadium | Preview |
