| 15 Jul 23 | r01  | Inverness CInverness C | 2 - 1 | Bonnyrigg Rose AthleticBonnyrigg Ros |
| 15 Jul 23 | r01 | KilmarnockKilmarnock | 3 - 0 | Annan AthleticAnnan Athleti |
| |
| 15 Jul 23 | r02 | StranraerStranraer | 1 - 5 | Ross CountyRoss County |
| 15 Jul 23 | r02 | Kelty HeartsKelty Hearts | 1 - 3 | MortonMorton |
| 15 Jul 23 | r02 | MontroseMontrose | 1 - 0 | St MirrenSt Mirren |
| 15 Jul 23 | r02 | ForfarForfar | 1 - 0 | CowdenbeathCowdenbeath |
| 15 Jul 23 | r02 | ClydeClyde | 1 - 3 | HamiltonHamilton |
| 15 Jul 23 | r02 | Brechin CityBrechin City | 0 - 3 | LivingstonLivingston |
| 15 Jul 23 | r02 | The SpartansThe Spartans | 1 - 0 | Dundee UnitedDundee United |
| 15 Jul 23 | r02 | Stirling AlbionStirling Albi | 1 - 1 | AyrAyr |
| 15 Jul 23 | r02 | StenhousemuirStenhousemuir | 1 - 0 | St JohnstoneSt Johnstone |
| |
| 15 Jul 23 | r01 | East FifeEast Fife | 0 - 0 | Queens ParkQueens Park |
| 15 Jul 23 | r01 | Elgin CityElgin City | 0 - 2 | MotherwellMotherwell |
| 15 Jul 23 | r01 | AirdrieoniansAirdrieonians | 2 - 0 | DumbartonDumbarton |
| |
| 15 Jul 23 | r02 | Peterhead FCPeterhead FC | 1 - 1 | PartickPartick |
| |
| 15 Jul 23 | r01  | Raith RvsRaith Rvs | 1 - 1 | DunfermlineDunfermline |
| |
| 18 Jul 23 | r04 | East FifeEast Fife | 3 - 1 | Elgin CityElgin City |
| 18 Jul 23 | r04 | Raith RvsRaith Rvs | 2 - 0 | Albion RoversAlbion Rovers |
| 18 Jul 23 | r04 | DunfermlineDunfermline | 4 - 0 | Annan AthleticAnnan Athleti |
| 18 Jul 23 | r04 | DumbartonDumbarton | 2 - 1 | Inverness CInverness C |
| 18 Jul 23 | r04 | Bonnyrigg Rose AthleticBonnyrigg Ros | 0 - 1 | Dundee FCDundee FC |
| 18 Jul 23 | r04 | Queen of SouthQueen of Sout | 3 - 3 | MotherwellMotherwell |
| 18 Jul 23 | r04 | MortonMorton | 3 - 0 | StranraerStranraer |
| 18 Jul 23 | r04 | MontroseMontrose | 1 - 2 | ForfarForfar |
| 18 Jul 23 | r04 | HamiltonHamilton | 1 - 0 | Brechin CityBrechin City |
| 18 Jul 23 | r04 | Cove RangersCove Rangers | 5 - 2 | ClydeClyde |
| |
| 18 Jul 23 | r03 | The SpartansThe Spartans | 1 - 2 | FalkirkFalkirk |
| 18 Jul 23 | r03 | Dundee UnitedDundee United | 1 - 2 | PartickPartick |
| 18 Jul 23 | r03 | AyrAyr | 1 - 0 | StenhousemuirStenhousemuir |
| 18 Jul 23 | r03 | AlloaAlloa | 1 - 2 | Stirling AlbionStirling Albi |
| |
| 19 Jul 23 | r05 | ArbroathArbroath | 1 - 1 | CowdenbeathCowdenbeath |
| 19 Jul 23 | r05 | Edinburgh CityEdinburgh Cit | 3 - 5 | Kelty HeartsKelty Hearts |
| |
| 22 Jul 23 | r06 | DunfermlineDunfermline | 0 - 2 | KilmarnockKilmarnock |
| 22 Jul 23 | r06 | Annan AthleticAnnan Athleti | 1 - 2 | Albion RoversAlbion Rovers |
| 22 Jul 23 | r06 | DumbartonDumbarton | 0 - 0 | Bonnyrigg Rose AthleticBonnyrigg Ros |
| 22 Jul 23 | r06 | AirdrieoniansAirdrieonians | 1 - 0 | Dundee FCDundee FC |
| 22 Jul 23 | r06 | Elgin CityElgin City | 0 - 2 | Queen of SouthQueen of Sout |
| 22 Jul 23 | r06 | StranraerStranraer | 2 - 1 | Edinburgh CityEdinburgh Cit |
| 22 Jul 23 | r06 | Ross CountyRoss County | 2 - 1 | MortonMorton |
| |
| 22 Jul 23 | r05 | CowdenbeathCowdenbeath | 1 - 1 | MontroseMontrose |
| 22 Jul 23 | r05 | LivingstonLivingston | 1 - 1 | HamiltonHamilton |
| 22 Jul 23 | r05 | Brechin CityBrechin City | 2 - 3 | Cove RangersCove Rangers |
| 22 Jul 23 | r05 | PartickPartick | 2 - 2 | FalkirkFalkirk |
| 22 Jul 23 | r05 | Dundee UnitedDundee United | 3 - 0 | Peterhead FCPeterhead FC |
| 22 Jul 23 | r05 | Stirling AlbionStirling Albi | 2 - 1 | StenhousemuirStenhousemuir |
| 22 Jul 23 | r05 | AlloaAlloa | 0 - 4 | St JohnstoneSt Johnstone |
| 22 Jul 23 | r05 | St MirrenSt Mirren | 4 - 0 | ArbroathArbroath |
| |
| 22 Jul 23 | r06 | MotherwellMotherwell | 1 - 0 | Queens ParkQueens Park |
| |
| 25 Jul 23 | r07 | Albion RoversAlbion Rovers | 0 - 3 | DunfermlineDunfermline |
| 25 Jul 23 | r07 | Inverness CInverness C | 2 - 3 | AirdrieoniansAirdrieonians |
| 25 Jul 23 | r07 | Queen of SouthQueen of Sout | 0 - 0 | East FifeEast Fife |
| 25 Jul 23 | r07 | Queens ParkQueens Park | 5 - 0 | Elgin CityElgin City |
| 25 Jul 23 | r07 | Kelty HeartsKelty Hearts | 2 - 0 | StranraerStranraer |
| 25 Jul 23 | r07 | ForfarForfar | 3 - 1 | ArbroathArbroath |
| 25 Jul 23 | r07 | Cove RangersCove Rangers | 0 - 5 | LivingstonLivingston |
| 25 Jul 23 | r07 | ClydeClyde | 1 - 2 | Brechin CityBrechin City |
| 25 Jul 23 | r07 | FalkirkFalkirk | 0 - 1 | Dundee UnitedDundee United |
| |
| 25 Jul 23 | r06 | StenhousemuirStenhousemuir | 1 - 3 | AlloaAlloa |
| 25 Jul 23 | r06 | St JohnstoneSt Johnstone | 1 - 2 | AyrAyr |
| |
| 25 Jul 23 | r07 | CowdenbeathCowdenbeath | 0 - 1 | St MirrenSt Mirren |
| |
| 26 Jul 23 | r08 | KilmarnockKilmarnock | 2 - 2 | Raith RvsRaith Rvs |
| 26 Jul 23 | r08 | Dundee FCDundee FC | 3 - 1 | DumbartonDumbarton |
| 26 Jul 23 | r08 | Edinburgh CityEdinburgh Cit | 1 - 3 | Ross CountyRoss County |
| 26 Jul 23 | r08 | Peterhead FCPeterhead FC | 1 - 2 | The SpartansThe Spartans |
| 29 Jul 23 | r08 | PartickPartick | 2 - 1 | The SpartansThe Spartans |
| |
| 29 Jul 23 | r09 | Annan AthleticAnnan Athleti | 2 - 3 | Raith RvsRaith Rvs |
| 29 Jul 23 | r09 | Albion RoversAlbion Rovers | 1 - 2 | KilmarnockKilmarnock |
| 29 Jul 23 | r09 | Bonnyrigg Rose AthleticBonnyrigg Ros | 0 - 1 | AirdrieoniansAirdrieonians |
| 29 Jul 23 | r09 | Queens ParkQueens Park | 1 - 2 | Queen of SouthQueen of Sout |
| 29 Jul 23 | r09 | MotherwellMotherwell | 3 - 0 | East FifeEast Fife |
| 29 Jul 23 | r09 | Ross CountyRoss County | 3 - 3 | Kelty HeartsKelty Hearts |
| 29 Jul 23 | r09 | MortonMorton | 4 - 1 | Edinburgh CityEdinburgh Cit |
| 29 Jul 23 | r09 | St MirrenSt Mirren | 4 - 0 | ForfarForfar |
| 29 Jul 23 | r09 | ArbroathArbroath | 3 - 0 | MontroseMontrose |
| |
| 29 Jul 23 | r08 | LivingstonLivingston | 1 - 0 | ClydeClyde |
| 29 Jul 23 | r08 | HamiltonHamilton | 2 - 2 | Cove RangersCove Rangers |
| 29 Jul 23 | r08 | FalkirkFalkirk | 4 - 1 | Peterhead FCPeterhead FC |
| 29 Jul 23 | r08 | St JohnstoneSt Johnstone | 0 - 4 | Stirling AlbionStirling Albi |
| 29 Jul 23 | r08 | AyrAyr | 6 - 0 | AlloaAlloa |
| |
| 30 Jul 23 | r09 | Dundee FCDundee FC | 1 - 0 | Inverness CInverness C |
| |
| 18 Aug 23 | r00 | Stirling AlbionStirling Albi | 1 - 2 | AberdeenAberdeen |
| 19 Aug 23 | r00 | RangersRangers | 2 - 1 | MortonMorton |
| 19 Aug 23 | r00 | AirdrieoniansAirdrieonians | 3 - 4 | Ross CountyRoss County |
| 19 Aug 23 | r00 | St MirrenSt Mirren | 1 - 0 | MotherwellMotherwell |
| 19 Aug 23 | r00 | LivingstonLivingston | 2 - 0 | AyrAyr |
| 20 Aug 23 | r00 | HibernianHibernian | 2 - 1 | Raith RvsRaith Rvs |
| 20 Aug 23 | r00 | HeartsHearts | 4 - 0 | PartickPartick |
| 20 Aug 23 | r00 | KilmarnockKilmarnock | 1 - 0 | CelticCeltic |
| 26 Sep 23 | r00 | KilmarnockKilmarnock | 1 - 2 | HeartsHearts |
| 27 Sep 23 | r00 | Ross CountyRoss County | 1 - 2 | AberdeenAberdeen |
| 27 Sep 23 | r00 | HibernianHibernian | 4 - 2 | St MirrenSt Mirren |
| 27 Sep 23 | r00 | RangersRangers | 4 - 0 | LivingstonLivingston |
| 04 Nov 23 | r00 | HibernianHibernian | 0 - 1 | AberdeenAberdeen |
| 05 Nov 23 | r00 | HeartsHearts | 1 - 3 | RangersRangers |
| 17 Dec 23 | r00 | RangersRangers | 1 - 0 | AberdeenAberdeen |
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