| 06 Oct 20 | r01  | MortonMorton | 2 - 2 | Queen of SouthQueen of Sout |
| 06 Oct 20 | r01 | East FifeEast Fife | 2 - 0 | CowdenbeathCowdenbeath |
| 06 Oct 20 | r01 | HeartsHearts | 1 - 0 | Inverness CInverness C |
| 06 Oct 20 | r01 | Dundee FCDundee FC | 3 - 0 | ForfarForfar |
| 06 Oct 20 | r01 | Edinburgh CityEdinburgh Cit | 1 - 5 | LivingstonLivingston |
| 06 Oct 20 | r01 | Stirling AlbionStirling Albi | 1 - 2 | ArbroathArbroath |
| 06 Oct 20 | r01 | DumbartonDumbarton | 0 - 1 | DunfermlineDunfermline |
| 06 Oct 20 | r01 | FalkirkFalkirk | 3 - 0 | KilmarnockKilmarnock |
| 06 Oct 20 | r01 | Albion RoversAlbion Rovers | 2 - 5 | AyrAyr |
| 06 Oct 20 | r01 | Annan AthleticAnnan Athleti | 3 - 1 | HamiltonHamilton |
| |
| 07 Oct 20 | r02 | HibernianHibernian | 3 - 1 | Brora RangersBrora Rangers |
| 07 Oct 20 | r02 | AirdrieoniansAirdrieonians | 0 - 2 | AlloaAlloa |
| 07 Oct 20 | r02 | St MirrenSt Mirren | 4 - 1 | PartickPartick |
| 07 Oct 20 | r02 | Brechin CityBrechin City | 2 - 6 | Dundee UnitedDundee United |
| 07 Oct 20 | r02 | MontroseMontrose | 3 - 3 | Ross CountyRoss County |
| 07 Oct 20 | r02 | Kelty HeartsKelty Hearts | 1 - 2 | St JohnstoneSt Johnstone |
| 09 Oct 20 | r02 | DunfermlineDunfermline | 2 - 0 | FalkirkFalkirk |
| 10 Oct 20 | r02 | Cove RangersCove Rangers | 1 - 2 | HibernianHibernian |
| |
| 10 Oct 20 | r03 | Brora RangersBrora Rangers | 0 - 2 | Dundee FCDundee FC |
| |
| 10 Oct 20 | r02 | LivingstonLivingston | 2 - 1 | AlloaAlloa |
| 10 Oct 20 | r02 | Edinburgh CityEdinburgh Cit | 2 - 2 | StenhousemuirStenhousemuir |
| |
| 10 Oct 20 | r03 | Queen of SouthQueen of Sout | 2 - 2 | St MirrenSt Mirren |
| 10 Oct 20 | r03 | PartickPartick | 2 - 0 | Queens ParkQueens Park |
| 10 Oct 20 | r03 | HamiltonHamilton | 2 - 1 | AyrAyr |
| 10 Oct 20 | r03 | Annan AthleticAnnan Athleti | 1 - 1 | StranraerStranraer |
| 10 Oct 20 | r03 | ClydeClyde | 3 - 2 | DumbartonDumbarton |
| 10 Oct 20 | r03 | Elgin CityElgin City | 2 - 0 | Stirling AlbionStirling Albi |
| 10 Oct 20 | r03 | ArbroathArbroath | 3 - 1 | MontroseMontrose |
| 10 Oct 20 | r03 | St JohnstoneSt Johnstone | 7 - 0 | Brechin CityBrechin City |
| 10 Oct 20 | r03 | Dundee UnitedDundee United | 0 - 1 | Peterhead FCPeterhead FC |
| |
| 10 Oct 20 | r04 | Raith RvsRaith Rvs | 2 - 1 | East FifeEast Fife |
| 10 Oct 20 | r04 | CowdenbeathCowdenbeath | 0 - 1 | HeartsHearts |
| 13 Oct 20 | r04 | Inverness CInverness C | 0 - 0 | CowdenbeathCowdenbeath |
| 13 Oct 20 | r04 | StranraerStranraer | 2 - 2 | Albion RoversAlbion Rovers |
| 13 Oct 20 | r04 | StenhousemuirStenhousemuir | 0 - 2 | AirdrieoniansAirdrieonians |
| 13 Oct 20 | r04 | AlloaAlloa | 2 - 1 | Edinburgh CityEdinburgh Cit |
| 13 Oct 20 | r04 | Queen of SouthQueen of Sout | 0 - 0 | PartickPartick |
| 13 Oct 20 | r04 | MortonMorton | 1 - 0 | Queens ParkQueens Park |
| 13 Oct 20 | r04 | AyrAyr | 1 - 0 | Annan AthleticAnnan Athleti |
| 13 Oct 20 | r04 | KilmarnockKilmarnock | 0 - 3 | DunfermlineDunfermline |
| |
| 13 Oct 20 | r05 | FalkirkFalkirk | 2 - 1 | ClydeClyde |
| 13 Oct 20 | r05 | MontroseMontrose | 0 - 2 | Elgin CityElgin City |
| 13 Oct 20 | r05 | Peterhead FCPeterhead FC | 3 - 1 | Brechin CityBrechin City |
| 13 Oct 20 | r05 | Dundee UnitedDundee United | 1 - 0 | Kelty HeartsKelty Hearts |
| 13 Oct 20 | r05 | ForfarForfar | 0 - 1 | HibernianHibernian |
| 13 Oct 20 | r05 | Brora RangersBrora Rangers | 2 - 2 | Cove RangersCove Rangers |
| 13 Oct 20 | r05 | HeartsHearts | 3 - 1 | Raith RvsRaith Rvs |
| 13 Oct 20 | r05 | Ross CountyRoss County | 2 - 1 | ArbroathArbroath |
| 10 Nov 20 | r05 | StenhousemuirStenhousemuir | 0 - 4 | LivingstonLivingston |
| |
| 10 Nov 20 | r06 | Elgin CityElgin City | 1 - 4 | Ross CountyRoss County |
| |
| 10 Nov 20 | r05  | Queens ParkQueens Park | 1 - 3 | Queen of SouthQueen of Sout |
| |
| 10 Nov 20 | r06 | Albion RoversAlbion Rovers | 1 - 5 | Annan AthleticAnnan Athleti |
| 10 Nov 20 | r06 | DumbartonDumbarton | 0 - 4 | FalkirkFalkirk |
| 10 Nov 20 | r06 | ClydeClyde | 0 - 2 | KilmarnockKilmarnock |
| 10 Nov 20 | r06 | Stirling AlbionStirling Albi | 2 - 1 | MontroseMontrose |
| 10 Nov 20 | r06 | St JohnstoneSt Johnstone | 0 - 0 | Dundee UnitedDundee United |
| 10 Nov 20 | r06 | Kelty HeartsKelty Hearts | 1 - 1 | Peterhead FCPeterhead FC |
| 10 Nov 20 | r06 | ForfarForfar | 3 - 3 | Brora RangersBrora Rangers |
| 10 Nov 20 | r06 | Dundee FCDundee FC | 3 - 0 | Cove RangersCove Rangers |
| 10 Nov 20 | r06 | Raith RvsRaith Rvs | 3 - 3 | Inverness CInverness C |
| |
| 10 Nov 20 | r07 | East FifeEast Fife | 2 - 3 | HeartsHearts |
| 11 Nov 20 | r07 | StranraerStranraer | 2 - 1 | HamiltonHamilton |
| 11 Nov 20 | r07 | St MirrenSt Mirren | 1 - 1 | MortonMorton |
| 11 Nov 20 | r07 | AirdrieoniansAirdrieonians | 0 - 1 | Edinburgh CityEdinburgh Cit |
| 14 Nov 20 | r07 | KilmarnockKilmarnock | 2 - 0 | DumbartonDumbarton |
| 14 Nov 20 | r07 | AyrAyr | 1 - 1 | StranraerStranraer |
| 14 Nov 20 | r07 | HamiltonHamilton | 3 - 0 | Albion RoversAlbion Rovers |
| |
| 14 Nov 20 | r08 | PartickPartick | 0 - 0 | MortonMorton |
| 14 Nov 20 | r08 | Queens ParkQueens Park | 0 - 1 | St MirrenSt Mirren |
| |
| 14 Nov 20 | r07 | AlloaAlloa | 4 - 2 | StenhousemuirStenhousemuir |
| |
| 14 Nov 20 | r08 | LivingstonLivingston | 4 - 1 | AirdrieoniansAirdrieonians |
| |
| 14 Nov 20 | r07 | Brechin CityBrechin City | 0 - 2 | Kelty HeartsKelty Hearts |
| 14 Nov 20 | r07 | Ross CountyRoss County | 3 - 0 | Stirling AlbionStirling Albi |
| |
| 14 Nov 20 | r08 | Peterhead FCPeterhead FC | 1 - 3 | St JohnstoneSt Johnstone |
| |
| 14 Nov 20 | r07 | Cove RangersCove Rangers | 1 - 0 | ForfarForfar |
| |
| 14 Nov 20 | r08 | Inverness CInverness C | 1 - 0 | East FifeEast Fife |
| |
| 14 Nov 20 | r07 | CowdenbeathCowdenbeath | 0 - 1 | Raith RvsRaith Rvs |
| 14 Nov 20 | r07 | DunfermlineDunfermline | 3 - 2 | ClydeClyde |
| |
| 14 Nov 20 | r08 | ArbroathArbroath | 3 - 0 | Elgin CityElgin City |
| 15 Nov 20 | r08 | HibernianHibernian | 4 - 1 | Dundee FCDundee FC |
| |
| 28 Nov 20 | r00 | LivingstonLivingston | 4 - 0 | AyrAyr |
| 28 Nov 20 | r00 | MotherwellMotherwell | 1 - 2 | St JohnstoneSt Johnstone |
| 28 Nov 20 | r00 | HibernianHibernian | 1 - 0 | Dundee FCDundee FC |
| 28 Nov 20 | r00 | ArbroathArbroath | 1 - 3 | DunfermlineDunfermline |
| 28 Nov 20 | r00 | AlloaAlloa | 1 - 0 | HeartsHearts |
| 28 Nov 20 | r00 | St MirrenSt Mirren | 2 - 1 | AberdeenAberdeen |
| 29 Nov 20 | r00 | CelticCeltic | 0 - 2 | Ross CountyRoss County |
| 29 Nov 20 | r00 | FalkirkFalkirk | 0 - 4 | RangersRangers |
| 15 Dec 20 | r00 | DunfermlineDunfermline | 1 - 1 | St JohnstoneSt Johnstone |
| 15 Dec 20 | r00 | AlloaAlloa | 1 - 2 | HibernianHibernian |
| 16 Dec 20 | r00 | LivingstonLivingston | 2 - 0 | Ross CountyRoss County |
| 16 Dec 20 | r00 | St MirrenSt Mirren | 3 - 2 | RangersRangers |
| 23 Jan 21 | r00 | St JohnstoneSt Johnstone | 3 - 0 | HibernianHibernian |
| 24 Jan 21 | r00 | LivingstonLivingston | 1 - 0 | St MirrenSt Mirren |
| 28 Feb 21 | r00 | LivingstonLivingston | 0 - 1 | St JohnstoneSt Johnstone |
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