| 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 | Hearts | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | ||
| 2 | 1 | Inverness CT | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | |
| 3 | 1 | Stirling Albion | 1 | 1 | 0 | 0 | 3 | 2 | +1 | 3 | W--- | |
| 4 | Cove Rangers | 2 | 0 | 0 | 2 | 2 | 6 | -4 | 0 | LL-- | ||
| 5 | Peterhead | 2 | 0 | 0 | 2 | 0 | 4 | -4 | 0 | LL-- | ||
| Tuesday, 13 July 2021 | |||||
| 2 | Hearts | 3-0 | Cove Rangers | ||
| 12 | Halliday | ||||
| 45 | Boyce | ||||
| 55 | Mackay-Steven | ||||
| 2 | Inverness CT | 2-0 | Peterhead | ||
| 50 | Duku | ||||
| 54 | Doran | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dundee United | 2 | 2 | 0 | 0 | 7 | 1 | +6 | 6 | WW-- | |
| 2 | 1 | Arbroath | 2 | 2 | 0 | 0 | 3 | 0 | +3 | 6 | WW-- | |
| 3 | 1 | Kelty Hearts | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 4 | 1 | East Fife | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | |
| 5 | Elgin City | 2 | 0 | 0 | 2 | 1 | 7 | -6 | 0 | LL-- | ||
| Wednesday, 14 July 2021 | |||||
| 2 | Dundee United | 6-1 | Elgin City | ||
| 19 | Shankland | 4 | Hester | ||
| 24 | Clark | ||||
| 32 | Shankland | ||||
| 40 | Pawlett | ||||
| 54 | Freeman | ||||
| 64 | Mochrie | ||||
| 2 | Arbroath | 2-0 | East Fife | ||
| 71 | Hilson | ||||
| 89 | Donnelly | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Forfar Athletic | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 5 | OW-- | |
| 2 | 1 | Montrose | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 | OW-- | |
| 3 | Dundee | 1 | 1 | 0 | 0 | 4 | 0 | +4 | 3 | W--- | ||
| 4 | 1 | Ross County | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 5 | 1 | Brora Rangers | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | |
| Tuesday, 13 July 2021 | |||||
| 2 | Dundee | 4-0 | Brora Rangers | ||
| 24 | McGowan | ||||
| 34 | McMullan | ||||
| 49 | McMullan | ||||
| 51 | Jakubiak | ||||
| 2 | Forfar Athletic | 0-0 | Montrose | ||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Raith Rovers | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | |
| 2 | 1 | Livingston | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 3 | 1 | Cowdenbeath | 2 | 1 | 0 | 1 | 1 | 1 | +0 | 3 | WL-- | |
| 4 | 1 | Alloa Athletic | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | Brechin City | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | ||
| Tuesday, 13 July 2021 | |||||
| 2 | Raith Rovers | 4-0 | Brechin City | ||
| 43 | Vaughan | ||||
| 62 | Spencer | ||||
| 66 | Zanatta | ||||
| 83 | Spencer | ||||
| 2 | Alloa Athletic | 0-1 | Cowdenbeath | ||
| 54 | Buchanan | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Ayr United | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 | WO-- | |
| 2 | 2 | Falkirk | 1 | 1 | 0 | 0 | 5 | 1 | +4 | 3 | W--- | |
| 3 | 2 | Hamilton | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 4 | 2 | Albion Rovers | 2 | 0 | 1 | 1 | 1 | 5 | -4 | 2 | LO-- | |
| 5 | FC Edinburgh | 2 | 0 | 0 | 2 | 0 | 4 | -4 | 0 | LL-- | ||
| Tuesday, 13 July 2021 | |||||
| 2 | Falkirk | 5-1 | Albion Rovers | ||
| 23 | Morrison | 11 | Wright | ||
| 29 | Morrison | ||||
| 36 | Dixon | ||||
| 85 | Telfer | ||||
| 87 | Weekes | ||||
| 2 | Ayr United | 3-0 | FC Edinburgh | ||
| 37 | Adeloye | ||||
| 49 | Adeloye | ||||
| 84 | Murdoch | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 4 | Queen of the South | 2 | 1 | 0 | 1 | 3 | 2 | +1 | 3 | WL-- | |
| 2 | 2 | Motherwell | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | 2 | Queen's Park | 2 | 1 | 0 | 1 | 1 | 1 | +0 | 3 | LW-- | |
| 4 | 2 | Annan Athletic | 2 | 0 | 1 | 1 | 2 | 4 | -2 | 2 | LX-- | |
| 5 | 2 | Airdrieonians | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| Tuesday, 13 July 2021 | |||||
| 2 | Annan Athletic | 1-3 | Queen of the South | ||
| 74 | Fleming | 29 | Paton | ||
| 49 | Roy | ||||
| 84 | Roy | ||||
| Wednesday, 14 July 2021 | |||||
| 2 | Queen's Park | 0-1 | Motherwell | ||
| 15 | Lawless | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Stranraer | 2 | 1 | 0 | 1 | 3 | 1 | +2 | 3 | LW-- | ||
| 2 | Kilmarnock | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | ||
| 3 | Clyde | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | ||
| 4 | 1 | Morton | 2 | 0 | 1 | 1 | 0 | 3 | -3 | 2 | OL-- | |
| 5 | 1 | East Kilbride | 2 | 0 | 1 | 1 | 0 | 2 | -2 | 1 | OL-- | |
| Tuesday, 13 July 2021 | |||||
| 2 | Clyde | 1-0 | Stranraer | ||
| 24(p) | Goodwillie | ||||
| 2 | Morton | 0-0 | East Kilbride | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | St.Mirren | 2 | 2 | 0 | 0 | 4 | 0 | +4 | 6 | WW-- | ||
| 2 | Dunfermline | 2 | 1 | 0 | 1 | 4 | 3 | +1 | 3 | LW-- | ||
| 3 | Stenhousemuir | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | ||
| 4 | Partick Thistle | 1 | 0 | 0 | 1 | 2 | 4 | -2 | 0 | L--- | ||
| 5 | Dumbarton | 2 | 0 | 0 | 2 | 1 | 5 | -4 | 0 | LL-- | ||
| Tuesday, 13 July 2021 | |||||
| 2 | St.Mirren | 1-0 | Dunfermline | ||
| 30 | Main | ||||
| 2 | Dumbarton | 1-2 | Stenhousemuir | ||
| 40 | MacLean | 63 | Lyon | ||
| 79 | Thomson | ||||
| 3 | +2 | Lawrence SHANKLAND (Dundee United) |
| 2 | +1 | Lewis VAUGHAN (Raith Rovers) |
| Nikolay TODOROV (Dunfermline) | ||
| +2 | Brad SPENCER (Raith Rovers) | |
| Nathan FLANAGAN (Stirling Albion) | ||
| +1 | Gary MACKAY-STEVEN (Hearts) | |
| +2 | Alistair ROY (Queen of the South) | |
| +2 | Callumn MORRISON (Falkirk) | |
| +2 | Tomi ADELOYE (Ayr United) | |
| +2 | Paul McMULLAN (Dundee) | |
| Fraser FYVIE (Cove Rangers) | ||
| +1 | Luke DONNELLY (Arbroath) | |
| +1 | Liam BOYCE (Hearts) |