| ROUND | R1 | R2 | QF | SF | F | ||||
| r1 | r2 | r3 | r4 | r5 | |||||
| Season archive |
| Group A | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | East Fife | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | |
| 2 | 1 | Hearts | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | 2 | Raith Rovers | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 2 | Inverness CT | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | Cowdenbeath | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| Tuesday, 6 October 2020 | |||||
| 1 | Hearts | 1-0 | Inverness CT | ||
| 62(p) | Walker | ||||
| 1 | East Fife | 2-0 | Cowdenbeath | ||
| 70 | Hamilton | ||||
| 82 | Wallace | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | ||
| 2 | 1 | Hibernian | 1 | 1 | 0 | 0 | 3 | 1 | +2 | 3 | W--- | |
| 3 | 1 | Cove Rangers | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | Brora Rangers | 1 | 0 | 0 | 1 | 1 | 3 | -2 | 0 | L--- | ||
| 5 | 3 | Forfar Athletic | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 1 | Dundee | 3-0 | Forfar Athletic | ||
| Score awarded as 3-0. | |||||
| Wednesday, 7 October 2020 | |||||
| 1 | Hibernian | 3-1 | Brora Rangers | ||
| 8 | Mallan | 61 | Gillespie | ||
| 12 | Mallan | ||||
| 89 | Hanlon | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dundee United | 1 | 1 | 0 | 0 | 6 | 2 | +4 | 3 | W--- | |
| 2 | 2 | St.Johnstone | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | |
| 3 | Peterhead | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 4 | 3 | Kelty Hearts | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | |
| 5 | Brechin City | 1 | 0 | 0 | 1 | 2 | 6 | -4 | 0 | L--- | ||
| Wednesday, 7 October 2020 | |||||
| 1 | Brechin City | 2-6 | Dundee United | ||
| 52(p) | Inglis | 15 | Clark | ||
| 54 | Currie | 18 | Clark | ||
| 40 | Butcher | ||||
| 47 | Harkes | ||||
| 60 | Smith | ||||
| 90 | Smith | ||||
| 1 | Kelty Hearts | 1-2 | St.Johnstone | ||
| 71 | Tidser | 45 | Kerr | ||
| 60 | Kane | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Arbroath | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | |
| 2 | 1 | Ross County | 1 | 0 | 1 | 0 | 3 | 3 | +0 | 2 | X--- | |
| 3 | Montrose | 1 | 0 | 1 | 0 | 3 | 3 | +0 | 1 | X--- | ||
| 4 | Elgin City | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 5 | Stirling Albion | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| Tuesday, 6 October 2020 | |||||
| 1 | Stirling Albion | 1-2 | Arbroath | ||
| 76 | Ryan | 14 | Donnelly | ||
| 32 | O'Brien | ||||
| Wednesday, 7 October 2020 | |||||
| 1 | Montrose | 3-3 | Ross County | ||
| 63 | Webster | 13 | Shaw | ||
| 67 | Ballantyne | 15 | McKay | ||
| 89 | Steeves | 52 | Charles-Cook | ||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Falkirk | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 2 | 1 | Dunfermline | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | 2 | Clyde | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | Dumbarton | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| 5 | 4 | Kilmarnock | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 1 | Falkirk | 3-0 | Kilmarnock | ||
| Score awarded as 3-0. | |||||
| 1 | Dumbarton | 0-1 | Dunfermline | ||
| 26(p) | O'Hara | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Ayr United | 1 | 1 | 0 | 0 | 5 | 2 | +3 | 3 | W--- | |
| 2 | 3 | Annan Athletic | 1 | 1 | 0 | 0 | 3 | 1 | +2 | 3 | W--- | |
| 3 | 1 | Stranraer | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 2 | Hamilton | 1 | 0 | 0 | 1 | 1 | 3 | -2 | 0 | L--- | |
| 5 | 3 | Albion Rovers | 1 | 0 | 0 | 1 | 2 | 5 | -3 | 0 | L--- | |
| Tuesday, 6 October 2020 | |||||
| 1 | Albion Rovers | 2-5 | Ayr United | ||
| 23(p) | Aitken | 30 | McCowan | ||
| 38 | Aitken | 35 | Walsh | ||
| 40 | Anderson | ||||
| 59 | Zanatta | ||||
| 82 | Anderson | ||||
| 1 | Annan Athletic | 3-1 | Hamilton | ||
| 31 | Swinglehurst | 51 | McMann | ||
| 38 | Fulton | ||||
| 43 | Purdue | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | St.Mirren | 1 | 1 | 0 | 0 | 4 | 1 | +3 | 3 | W--- | |
| 2 | 1 | Queen of the South | 1 | 0 | 1 | 0 | 2 | 2 | +0 | 2 | X--- | |
| 3 | 1 | Morton | 1 | 0 | 1 | 0 | 2 | 2 | +0 | 1 | X--- | |
| 4 | Queen's Park | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 5 | 4 | Partick Thistle | 1 | 0 | 0 | 1 | 1 | 4 | -3 | 0 | L--- | |
| Tuesday, 6 October 2020 | |||||
| 1 | Morton | 2-2 | Queen of the South | ||
| 18 | McGinty | 53 | Dobbie | ||
| 68 | Nesbitt | 79 | Shields | ||
| Wednesday, 7 October 2020 | |||||
| 1 | St.Mirren | 4-1 | Partick Thistle | ||
| 45 | Tait | 66 | Spittal | ||
| 74 | Obika | ||||
| 81(og) | Breen | ||||
| 82 | Connolly | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 1 | 1 | 0 | 0 | 5 | 1 | +4 | 3 | W--- | ||
| 2 | Alloa Athletic | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | ||
| 3 | 1 | Stenhousemuir | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 1 | Airdrieonians | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | |
| 5 | FC Edinburgh | 1 | 0 | 0 | 1 | 1 | 5 | -4 | 0 | L--- | ||
| Tuesday, 6 October 2020 | |||||
| 1 | FC Edinburgh | 1-5 | Livingston | ||
| 70(p) | Handling | 7 | Robinson | ||
| 22 | Mullin | ||||
| 40 | Mullin | ||||
| 65 | Poplatnik | ||||
| 77 | Lokotsch | ||||
| Wednesday, 7 October 2020 | |||||
| 1 | Airdrieonians | 0-2 | Alloa Athletic | ||
| 14(p) | Trouten | ||||
| 69 | Thomson | ||||
| 2 | +2 | Stevie MALLAN (Hibernian) |
| +2 | Bruce ANDERSON (Ayr United) | |
| +2 | Cammy SMITH (Dundee United) | |
| +2 | Josh MULLIN (Livingston) | |
| +2 | Nicky CLARK (Dundee United) | |
| +2 | Matty AITKEN (Albion Rovers, 1p) |