| 19 Oct 19 | r00  | Annan AthleticAnnan Athleti | 2 - 2 | Brechin CityBrechin City |
| 19 Oct 19 | r00 | Elgin CityElgin City | 3 - 1 | Berwick RangersBerwick Range |
| 26 Oct 19 | r00 | Brechin CityBrechin City | 0 - 2 | Annan AthleticAnnan Athleti |
| 23 Nov 19 | r00 | StranraerStranraer | 1 - 0 | DunfermlineDunfermline |
| 23 Nov 19 | r00 | DumbartonDumbarton | 3 - 1 | ForfarForfar |
| 23 Nov 19 | r00 | Elgin CityElgin City | 1 - 3 | AlloaAlloa |
| 23 Nov 19 | r00 | Albion RoversAlbion Rovers | 1 - 4 | AirdrieoniansAirdrieonians |
| 23 Nov 19 | r00 | Queen of SouthQueen of Sout | 1 - 2 | Queens ParkQueens Park |
| 23 Nov 19 | r00 | Edinburgh CityEdinburgh Cit | 4 - 3 | Annan AthleticAnnan Athleti |
| 23 Nov 19 | r00 | Stirling AlbionStirling Albi | 0 - 2 | ClydeClyde |
| 23 Nov 19 | r00 | Raith RvsRaith Rvs | 1 - 0 | Peterhead FCPeterhead FC |
| 23 Nov 19 | r00 | MortonMorton | 1 - 1 | Brora RangersBrora Rangers |
| 03 Dec 19 | r00 | Brora RangersBrora Rangers | 1 - 3 | MortonMorton |
| |
| 17 Jan 20 | r04 | RangersRangers | 2 - 0 | StranraerStranraer |
| 18 Jan 20 | r04 | St JohnstoneSt Johnstone | 3 - 0 | MortonMorton |
| 18 Jan 20 | r04 | AberdeenAberdeen | 1 - 0 | DumbartonDumbarton |
| 18 Jan 20 | r04 | AlloaAlloa | 2 - 3 | Inverness CInverness C |
| 18 Jan 20 | r04 | ArbroathArbroath | 0 - 0 | FalkirkFalkirk |
| 18 Jan 20 | r04 | AyrAyr | 1 - 0 | Ross CountyRoss County |
| 18 Jan 20 | r04 | HamiltonHamilton | 5 - 0 | Edinburgh CityEdinburgh Cit |
| 18 Jan 20 | r04 | HeartsHearts | 5 - 0 | AirdrieoniansAirdrieonians |
| 18 Jan 20 | r04 | KilmarnockKilmarnock | 6 - 0 | Queens ParkQueens Park |
| 18 Jan 20 | r04 | LivingstonLivingston | 3 - 1 | Raith RvsRaith Rvs |
| 18 Jan 20 | r04 | PartickPartick | 1 - 2 | CelticCeltic |
| 18 Jan 20 | r04 | Dundee FCDundee FC | 0 - 3 | MotherwellMotherwell |
| 19 Jan 20 | r04 | Dundee UnitedDundee United | 2 - 2 | HibernianHibernian |
| 28 Jan 20 | r04 | FalkirkFalkirk | 2 - 0 | ArbroathArbroath |
| 28 Jan 20 | r04 | HibernianHibernian | 4 - 2 | Dundee UnitedDundee United |
| |
| 08 Feb 20 | r05 | HamiltonHamilton | 1 - 4 | RangersRangers |
| 08 Feb 20 | r05 | AyrAyr | 1 - 2 | St JohnstoneSt Johnstone |
| 08 Feb 20 | r05 | AberdeenAberdeen | 0 - 0 | KilmarnockKilmarnock |
| 08 Feb 20 | r05 | Inverness CInverness C | 1 - 0 | LivingstonLivingston |
| 08 Feb 20 | r05 | St MirrenSt Mirren | 1 - 1 | MotherwellMotherwell |
| 08 Feb 20 | r05 | FalkirkFalkirk | 0 - 1 | HeartsHearts |
| 09 Feb 20 | r05 | ClydeClyde | 0 - 3 | CelticCeltic |
| 18 Feb 20 | r05 | MotherwellMotherwell | 4 - 4 | St MirrenSt Mirren |
| 19 Feb 20 | r05 | KilmarnockKilmarnock | 3 - 4 | AberdeenAberdeen |
| |
| 28 Feb 20 | r00 | HibernianHibernian | 5 - 2 | Inverness CInverness C |
| 29 Feb 20 | r00 | HeartsHearts | 1 - 0 | RangersRangers |
| 29 Feb 20 | r00 | St MirrenSt Mirren | 0 - 2 | AberdeenAberdeen |
| 01 Mar 20 | r00 | St JohnstoneSt Johnstone | 0 - 1 | CelticCeltic |
| 31 Oct 20 | r00 | HeartsHearts | 2 - 1 | HibernianHibernian |
| 01 Nov 20 | r00 | CelticCeltic | 2 - 0 | AberdeenAberdeen |
| 20 Dec 20 | r00   | CelticCeltic | 3 - 3 | HeartsHearts |
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