| 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 | 1 | Hearts | 2 | 2 | 0 | 0 | 2 | 0 | +2 | 6 | WW-- | |
| 2 | 1 | East Fife | 2 | 1 | 0 | 1 | 3 | 2 | +1 | 3 | LW-- | |
| 3 | Raith Rovers | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | ||
| 4 | Inverness CT | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| 5 | Cowdenbeath | 2 | 0 | 0 | 2 | 0 | 3 | -3 | 0 | LL-- | ||
| Saturday, 10 October 2020 | |||||
| 2 | Raith Rovers | 2-1 | East Fife | ||
| 45(p) | Hendry | 15 | Newton | ||
| 87 | Duku | ||||
| 2 | Cowdenbeath | 0-1 | Hearts | ||
| 78 | Halkett | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | ||
| 2 | Hibernian | 2 | 2 | 0 | 0 | 5 | 2 | +3 | 6 | WW-- | ||
| 3 | Cove Rangers | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| 4 | 1 | Forfar Athletic | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 5 | 1 | Brora Rangers | 2 | 0 | 0 | 2 | 1 | 5 | -4 | 0 | LL-- | |
| Saturday, 10 October 2020 | |||||
| 2 | Cove Rangers | 1-2 | Hibernian | ||
| 17 | Higgins | 49 | Gullan | ||
| 60 | Nisbet | ||||
| 2 | Brora Rangers | 0-2 | Dundee | ||
| 11 | Dorrans | ||||
| 27 | Mullen | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | St.Johnstone | 2 | 2 | 0 | 0 | 9 | 1 | +8 | 6 | WW-- | |
| 2 | 1 | Dundee United | 2 | 1 | 0 | 1 | 6 | 3 | +3 | 3 | LW-- | |
| 3 | Peterhead | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | ||
| 4 | Kelty Hearts | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| 5 | Brechin City | 2 | 0 | 0 | 2 | 2 | 13 | -11 | 0 | LL-- | ||
| Saturday, 10 October 2020 | |||||
| 2 | St.Johnstone | 7-0 | Brechin City | ||
| 3 | May | ||||
| 25 | Wotherspoon | ||||
| 56 | Wotherspoon | ||||
| 58 | May | ||||
| 62 | May | ||||
| 88(p) | Hendry | ||||
| 90 | Davidson | ||||
| 2 | Dundee United | 0-1 | Peterhead | ||
| 51 | Boyd | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Arbroath | 2 | 2 | 0 | 0 | 5 | 2 | +3 | 6 | WW-- | ||
| 2 | 2 | Elgin City | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | |
| 3 | 1 | Ross County | 1 | 0 | 1 | 0 | 3 | 3 | +0 | 2 | X--- | |
| 4 | 1 | Montrose | 2 | 0 | 1 | 1 | 4 | 6 | -2 | 1 | LX-- | |
| 5 | Stirling Albion | 2 | 0 | 0 | 2 | 1 | 4 | -3 | 0 | LL-- | ||
| Saturday, 10 October 2020 | |||||
| 2 | Arbroath | 3-1 | Montrose | ||
| 27 | Swankie | 10 | Webster | ||
| 43 | Thomson | ||||
| 86 | O'Brien | ||||
| 2 | Elgin City | 2-0 | Stirling Albion | ||
| 67 | Hester | ||||
| 81(p) | Dingwall | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dunfermline | 2 | 2 | 0 | 0 | 3 | 0 | +3 | 6 | WW-- | |
| 2 | 1 | Clyde | 1 | 1 | 0 | 0 | 3 | 2 | +1 | 3 | W--- | |
| 3 | 2 | Falkirk | 2 | 1 | 0 | 1 | 3 | 2 | +1 | 3 | LW-- | |
| 4 | Dumbarton | 2 | 0 | 0 | 2 | 2 | 4 | -2 | 0 | LL-- | ||
| 5 | Kilmarnock | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| Friday, 9 October 2020 | |||||
| 2 | Dunfermline | 2-0 | Falkirk | ||
| 58 | Murray | ||||
| 65 | Murray | ||||
| Saturday, 10 October 2020 | |||||
| 2 | Clyde | 3-2 | Dumbarton | ||
| 10 | Cuddihy | 40 | Hamilton | ||
| 22(p) | Goodwillie | 55 | Jones | ||
| 45 | Cunningham | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Annan Athletic | 2 | 1 | 1 | 0 | 4 | 2 | +2 | 4 | XW-- | |
| 2 | 1 | Ayr United | 2 | 1 | 0 | 1 | 6 | 4 | +2 | 3 | LW-- | |
| 3 | 1 | Hamilton | 2 | 1 | 0 | 1 | 3 | 4 | -1 | 3 | WL-- | |
| 4 | 1 | Stranraer | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | |
| 5 | Albion Rovers | 1 | 0 | 0 | 1 | 2 | 5 | -3 | 0 | L--- | ||
| Saturday, 10 October 2020 | |||||
| 2 | Hamilton | 2-1 | Ayr United | ||
| 19 | Ogboe | 68 | Moffat | ||
| 36 | Trafford | ||||
| 2 | Annan Athletic | 1-1 | Stranraer | ||
| 55 | Moxon | 37 | Paton | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | St.Mirren | 2 | 1 | 1 | 0 | 6 | 3 | +3 | 5 | XW-- | ||
| 2 | Queen of the South | 2 | 0 | 2 | 0 | 4 | 4 | +0 | 3 | XX-- | ||
| 3 | 2 | Partick Thistle | 2 | 1 | 0 | 1 | 3 | 4 | -1 | 3 | WL-- | |
| 4 | 1 | Morton | 1 | 0 | 1 | 0 | 2 | 2 | +0 | 1 | X--- | |
| 5 | 1 | Queen's Park | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | |
| Saturday, 10 October 2020 | |||||
| 2 | Partick Thistle | 2-0 | Queen's Park | ||
| 66 | Cardle | ||||
| 81 | Cardle | ||||
| 2 | Queen of the South | 2-2 | St.Mirren | ||
| 8 | Shields | 51 | McGrath | ||
| 12 | Fitzpatrick | 89 | Fraser | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 2 | 2 | 0 | 0 | 7 | 2 | +5 | 6 | WW-- | ||
| 2 | Alloa Athletic | 2 | 1 | 0 | 1 | 3 | 2 | +1 | 3 | LW-- | ||
| 3 | Stenhousemuir | 1 | 0 | 1 | 0 | 2 | 2 | +0 | 2 | X--- | ||
| 4 | 1 | FC Edinburgh | 2 | 0 | 1 | 1 | 3 | 7 | -4 | 1 | XL-- | |
| 5 | 1 | Airdrieonians | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | |
| Saturday, 10 October 2020 | |||||
| 2 | Livingston | 2-1 | Alloa Athletic | ||
| 46 | Forrest | 31 | Thomson | ||
| 50 | Mullin | ||||
| 2 | FC Edinburgh | 2-2 | Stenhousemuir | ||
| 43 | Henderson | 9 | Bia-Bi | ||
| 52 | De Vita | 85 | Tapping | ||
| 3 | +1 | Josh MULLIN (Livingston) |
| +3 | Stevie MAY (St.Johnstone) | |
| 2 | +2 | Euan MURRAY (Dunfermline) |
| +1 | Robert THOMSON (Alloa Athletic) | |
| +1 | Graham WEBSTER (Montrose) | |
| Stevie MALLAN (Hibernian) | ||
| Bruce ANDERSON (Ayr United) | ||
| +2 | David WOTHERSPOON (St.Johnstone) | |
| +1 | Connor SHIELDS (Queen of the South) | |
| Cammy SMITH (Dundee United) | ||
| Nicky CLARK (Dundee United) | ||
| Matty AITKEN (Albion Rovers, 1p) | ||
| +1 | Thomas O'BRIEN (Arbroath) | |
| +2 | Joe CARDLE (Partick Thistle) |