2nd Round: 28 October 2023 | ||
|---|---|---|
| Beith Juniors | v | Broomhill |
| Brechin City | v | The Spartans |
| Civil Service Strollers | v | Stranraer |
| Cumnock Juniors | v | Turriff United |
| Deveronvale | v | Broxburn Athletic |
| Dumbarton | v | Banks O’Dee |
| Dunbar United | v | East Fife |
| Formartine United | v | Clydebank |
| Forres Mechanics | v | Buckie Thistle |
| Fraserburgh | v | Bonnyrigg Rose |
| Huntly | v | Forfar Athletic |
| Jeanfield Swifts | v | Elgin City |
| Kilwinning Rangers | v | Cowdenbeath |
| Luncarty | v | Bo’ness United |
| Musselburgh Athletic | v | Clyde |
| Peterhead | v | Clachnacuddin |
| Pollok | v | Gala Fairydean Rovers |
| Stenhousemuir | v | Brora Rangers |
| Tranent | v | East Kilbride |
| University of Stirling or Albion Rovers | v | St Andrews United |
1st Round: 23-25 September 2023 | ||
| Banks o’ Dee | 6:0 | Dalbeattie Star |
| Bo’ness United | 3:0 | Darvel |
| Brechin City | 4:0 | Rothes |
| Broomhill | 3:1 | Cumbernauld Colts |
| Brora Rangers | 5:1 | Berwick Rangers |
| Broxburn Athletic | 2:1 | Nairn County |
| Caledonian Braves | 1:2 | Fraserburgh |
| Camelon Juniors | 1:2 | Civil Service Strollers |
| Clachnacuddin | 1:0 | Inverurie Loco Works |
| Cowdenbeath | 2:1 | Linlithgow Rose |
| Culter | 3:4 | Deveronvale |
| Dalkeith Thistle | 0:7 | Clydebank |
| Dundonald Bluebell | 2:3 | Kilwinning Rangers |
| Dunipace | 1:3 | Cumnock Juniors |
| East Kilbride | 8:0 | Whitehill Welfare |
| East Stirlingshire | 0:1 | Huntly |
| Edinburgh University | 2:3 | Dunbar United |
| Formartine United | 3:2 | Threave Rovers |
| Gala Fairydean Rovers | 8:2 | Strathspey Thistle |
| Golspie Sutherland | 1:1(7-8p) | Forres Mechanics |
| Keith | 2:5 | Luncarty |
| Lossiemouth | 0:4 | Beith Juniors |
| Musselburgh Athletic | 1:1(4-3p) | Gretna 2008 |
| Penicuik Athletic | 0:6 | Pollok |
| St Andrews United | 1:0 | Auchinleck Talbot |
| Tayport | 0:4 | Buckie Thistle |
| Tranent Juniors | 4:1 | Hutchison Vale |
| Turriff United | 2:1 | Sauchie Juniors |
| Wick Academy | 1:3 | Jeanfield Swifts |
| Stirling University | v | Albion Rovers |
Preliminary Round 2: 2 September 2023 | ||
| Beith Juniors | 5-1 | Bonnyton Thistle |
| Broxburn Athletic | 3-0 | Lochee United |
| Camelon Juniors | 0-0(4-3p) | Newtongrange Star |
| Carluke Rovers | 2-3 | Dalbeattie Star |
| Creetown | 1-3 | Whitehill Welfare |
| Culter | 3-2 | Blackburn United |
| Cumnock Juniors | 1-0 | Girvan |
| Dunbar United | 4-2 | Vale of Leithen |
| Easthouses Lily | 1-3 | Threave Rovers |
| Fort William | 1-10 | Clydebank |
| Glenafton Athletic | 0-3 | Darvel |
| Hawick Royal Albert | 1-2 | Golspie Sutherland |
| Hill of Beath Hawthorn | 0-1 | Tayport |
| Irvine Meadow XI | 1-2 | Dunipace |
| Jeanfield Swifts | 3-0 | Cupar Hearts AFC |
| Kilwinning Rangers | 4-0 | Glasgow University |
| Musselburgh Athletic | 6-0 | Coldstream |
| Newton Stewart | 1-4 | Luncarty |
| Penicuik Athletic | 4-2 | Rutherglen Glencairn |
| Pollok | 2-2(3-0p) | Benburb |
| Preston Athletic | 0-0(4-5p) | Dundonald Bluebell |
| Sauchie Juniors | 4-0 | Burntisland Shipyard |
| St Andrews United | 1-0 | Haddington Athletic |
| St Cuthbert Wanderers | 0-5 | Dalkeith Thistle |
| Tynecastle | 0-1 | Hutchison Vale |
| Wigtown & Bladnoch | 0-12 | Auchinleck Talbot |
Preliminary Round 1: 12 August 2023 | ||
| Abbey Vale | 0-5 | Cupar Hearts |
| Carnoustie Panmure | 1-2 | Beith Juniors |
| Luncarty | 3-1 | Loch Ness |
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