| 21.09.2019 | |||
| 16:00 | Broxburn Athletic | 3-2 | East Stirlingshire |
| 16:00 | Buckie Thistle | 4-1 | Civil Service Strollers |
| 16:00 | Caledonian Braves | 3-4 | Rothes FC |
| 16:00 | Cumbernauld Colts | 1-5 | Penicuik Athletic |
| 16:00 | Dalbeattie Star | 1-3 | Gala Fairydean |
| 16:00 | Edinburgh Univ AFC | 1-3 | Lochee United |
| 16:00 | Forres Mechanics | 1-4 | Banks O' Dee |
| 16:00 | Fort William | 5-0 | Vale of Leithen |
| 16:00 | Fraserburgh FC | 0-1 | Bonnyrigg Rose |
| 16:00 | Gretna 2008 | 1-0 | Hill of Beath FC |
| 16:00 | Inverurie Loco Works | 3-2 | Wick Academy |
| 16:00 | Keith FC | 2-3 | Stirling University |
| 16:00 | Linlithgow Rose | 1-0 | Huntly FC |
| 16:00 | Nairn County | 0-0 | Clachnacuddin |
| 16:00 | Spartans FC | 1-1 | Deveronvale FC |
| 16:00 | Strathspey Thistle | 2-1 | Lossiemouth FC |
| 16:00 | Turriff United | 1-5 | Formartine United |
| 20.09.2019 | |||
| 20:05 | Kelty Hearts | 0-3 | Auchinleck Talbot |
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