| 02 Sep 23 |
r00  | Tynecastle F.C.Tynecastle F. | 0 - 1 | Lothian Thistle HutchisonLothian Thist |
| 02 Sep 23 |
r00 | Preston Athletic F.C.Preston Athle | 0 - 0 | Dundonald Bluebell F.C.Dundonald Blu |
| 02 Sep 23 |
r00 | Musselburgh Athletic F.C.Musselburgh A | 6 - 0 | Coldstream F.C.Coldstream F. |
| 02 Sep 23 |
r00 | Easthouses Lily Miners WeEasthouses Li | 1 - 3 | Threave Rovers F.C.Threave Rover |
| 02 Sep 23 |
r00 | Camelon Juniors F.C.Camelon Junio | 0 - 0 | Newtongrange Star F.C.Newtongrange |
| 23 Sep 23 |
r00 | East StirlingshireEast Stirling | 0 - 1 | HuntlyHuntly |
| 23 Sep 23 |
r00 | Formartine UnitedFormartine Un | 3 - 2 | Threave Rovers F.C.Threave Rover |
| 23 Sep 23 |
r00 | Gala Fairydean RoversGala Fairydea | 8 - 2 | Strathspey ThistleStrathspey Th |
| 23 Sep 23 |
r00 | Musselburgh Athletic F.C.Musselburgh A | 1 - 1 | Gretna 2008Gretna 2008 |
| 23 Sep 23 |
r00 | Tranent Juniors F.C.Tranent Junio | 4 - 1 | Lothian Thistle HutchisonLothian Thist |
| 23 Sep 23 |
r00 | Wick AcademyWick Academy | 1 - 3 | Jeanfield Swifts F.C.Jeanfield Swi |
| 23 Sep 23 |
r00 | East KilbrideEast Kilbride | 8 - 0 | Whitehill Welfare F.C.Whitehill Wel |
| 23 Sep 23 |
r00 | CowdenbeathCowdenbeath | 2 - 1 | Linlithgow Rose F.C.Linlithgow Ro |
| 23 Sep 23 |
r00 | ClachnacuddinClachnacuddin | 1 - 0 | Inverurie Loco WorksInverurie Loc |
| 23 Sep 23 |
r00 | Camelon Juniors F.C.Camelon Junio | 1 - 2 | Civil Service StrollersCivil Service |
| 23 Sep 23 |
r00 | Caledonian BravesCaledonian Br | 1 - 2 | FraserburghFraserburgh |
| 23 Sep 23 |
r00 | Broxburn Athletic F.C.Broxburn Athl | 2 - 1 | Nairn CountyNairn County |
| 23 Sep 23 |
r00 | Brora RangersBrora Rangers | 5 - 1 | Berwick RangersBerwick Range |
| 23 Sep 23 |
r00 | Banks O Dee F.C.Banks O Dee F | 6 - 0 | Dalbeattie StarDalbeattie St |
| 24 Sep 23 |
r00 | BroomhillBroomhill | 3 - 1 | Cumbernauld ColtsCumbernauld C |
| 25 Sep 23 |
r00 | University of StirlingUniversity of | 1 - 3 | Albion RoversAlbion Rovers |
| 28 Oct 23 |
r00 | Jeanfield Swifts F.C.Jeanfield Swi | 6 - 0 | Elgin CityElgin City |
| 28 Oct 23 |
r00 | Peterhead FCPeterhead FC | 3 - 1 | ClachnacuddinClachnacuddin |
| 28 Oct 23 |
r00 | StenhousemuirStenhousemuir | 0 - 2 | Brora RangersBrora Rangers |
| 28 Oct 23 |
r00 | Tranent Juniors F.C.Tranent Junio | 7 - 0 | East KilbrideEast Kilbride |
| 28 Oct 23 |
r00 | FraserburghFraserburgh | 1 - 2 | Bonnyrigg Rose AthleticBonnyrigg Ros |
| 28 Oct 23 |
r00 | Forres MechanicsForres Mechan | 0 - 1 | Buckie ThistleBuckie Thistl |
| 28 Oct 23 |
r00 | DumbartonDumbarton | 3 - 2 | Banks O Dee F.C.Banks O Dee F |
| 28 Oct 23 |
r00 | DeveronvaleDeveronvale | 0 - 1 | Broxburn Athletic F.C.Broxburn Athl |
| 28 Oct 23 |
r00 | Civil Service StrollersCivil Service | 0 - 3 | StranraerStranraer |
| 30 Oct 23 |
r00 | Musselburgh Athletic F.C.Musselburgh A | 2 - 3 | ClydeClyde |
| 24 Nov 23 |
r00 | ClydeClyde | 2 - 0 | Jeanfield Swifts F.C.Jeanfield Swi |
| 25 Nov 23 |
r00 | Tranent Juniors F.C.Tranent Junio | 0 - 1 | ForfarForfar |
| 25 Nov 23 |
r00 | StranraerStranraer | 0 - 1 | AirdrieoniansAirdrieonians |
| 25 Nov 23 |
r00 | Stirling AlbionStirling Albi | 0 - 2 | Cove RangersCove Rangers |
| 25 Nov 23 |
r00 | Queen of SouthQueen of Sout | 2 - 2 | Dundee UnitedDundee United |
| 25 Nov 23 |
r00 | MontroseMontrose | 3 - 0 | Edinburgh CityEdinburgh Cit |
| 25 Nov 23 |
r00 | FalkirkFalkirk | 3 - 0 | Formartine UnitedFormartine Un |
| 25 Nov 23 |
r00 | Broxburn Athletic F.C.Broxburn Athl | 2 - 2 | Buckie ThistleBuckie Thistl |
| 25 Nov 23 |
r00 | Annan AthleticAnnan Athleti | 4 - 5 | DumbartonDumbarton |
| 25 Nov 23 |
r00 | Albion RoversAlbion Rovers | 0 - 1 | Bonnyrigg Rose AthleticBonnyrigg Ros |
| 25 Nov 23 |
r00 | MortonMorton | 4 - 0 | Boness UnitedBoness United |
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