| 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 | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | ||
| 2 | 2 | Stirling Albion | 1 | 1 | 0 | 0 | 3 | 2 | +1 | 3 | W--- | |
| 3 | Inverness CT | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 4 | 1 | Cove Rangers | 1 | 0 | 0 | 1 | 2 | 3 | -1 | 0 | L--- | |
| 5 | 2 | Peterhead | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | |
| Saturday, 10 July 2021 | |||||
| 1 | Peterhead | 0-2 | Hearts | ||
| 31 | Mackay-Steven | ||||
| 58 | Boyce | ||||
| 1 | Cove Rangers | 2-3 | Stirling Albion | ||
| 69 | Fyvie | 28 | Omar | ||
| 82 | Fyvie | 55 | Flanagan | ||
| 90 | Flanagan | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Arbroath | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 2 | Dundee United | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | ||
| 3 | 1 | East Fife | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | Kelty Hearts | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| 5 | 2 | Elgin City | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Friday, 9 July 2021 | |||||
| 1 | Kelty Hearts | 0-1 | Dundee United | ||
| 77 | Shankland | ||||
| Saturday, 10 July 2021 | |||||
| 1 | Elgin City | 0-1 | Arbroath | ||
| 80 | Donnelly | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 4 | Montrose | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 2 | 3 | Forfar Athletic | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 3 | 1 | Dundee | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | Brora Rangers | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| 5 | 4 | Ross County | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 1 | Forfar Athletic | 3-0 | Ross County | ||
| Score awarded as 3-0. | |||||
| 1 | Montrose | 3-0 | Brora Rangers | ||
| 20 | Rennie | ||||
| 22 | Lyons | ||||
| 88(p) | Milne | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | ||
| 2 | Raith Rovers | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | ||
| 3 | 1 | Alloa Athletic | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 1 | Cowdenbeath | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | Brechin City | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| Saturday, 10 July 2021 | |||||
| 1 | Cowdenbeath | 0-1 | Raith Rovers | ||
| 21 | Vaughan | ||||
| 1 | Brechin City | 0-3 | Livingston | ||
| 1 | Parkes | ||||
| 61 | Obileye | ||||
| 90 | Longridge | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 3 | Hamilton | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 2 | 3 | Albion Rovers | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 2 | O--- | |
| 3 | 2 | Ayr United | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 1 | O--- | |
| 4 | 2 | Falkirk | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 5 | 2 | FC Edinburgh | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Friday, 9 July 2021 | |||||
| 1 | FC Edinburgh | 0-1 | Hamilton | ||
| 25 | Smith | ||||
| Saturday, 10 July 2021 | |||||
| 1 | Albion Rovers | 0-0 | Ayr United | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 4 | Queen's Park | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 2 | Annan Athletic | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | ||
| 3 | 1 | Airdrieonians | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| 4 | 3 | Motherwell | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 5 | 3 | Queen of the South | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Saturday, 10 July 2021 | |||||
| 1 | Airdrieonians | 1-1 | Annan Athletic | ||
| 90 | McDonald | 67(p) | Wallace | ||
| 1 | Queen of the South | 0-1 | Queen's Park | ||
| 54 | Biggar | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Stranraer | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 2 | 1 | Kilmarnock | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | |
| 3 | 1 | Clyde | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | East Kilbride | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| 5 | 1 | Morton | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| 1 | Stranraer | 3-0 | Morton | ||
| Score awarded as 3-0. | |||||
| 1 | East Kilbride | 0-2 | Kilmarnock | ||
| 49 | Murray | ||||
| 62 | Naismith | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | St.Mirren | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | ||
| 2 | 1 | Dunfermline | 1 | 1 | 0 | 0 | 4 | 2 | +2 | 3 | W--- | |
| 3 | 2 | Stenhousemuir | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 1 | Partick Thistle | 1 | 0 | 0 | 1 | 2 | 4 | -2 | 0 | L--- | |
| 5 | Dumbarton | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| Saturday, 10 July 2021 | |||||
| 1 | Partick Thistle | 2-4 | Dunfermline | ||
| 16 | Graham | 30 | Todorov | ||
| 64 | Rudden | 35 | Comrie | ||
| 43 | MacDonald | ||||
| 53 | Todorov | ||||
| 1 | Dumbarton | 0-3 | St.Mirren | ||
| Score awarded as 0-3. | |||||
| 2 | +2 | Nikolay TODOROV (Dunfermline) |
| +2 | Nathan FLANAGAN (Stirling Albion) | |
| +2 | Fraser FYVIE (Cove Rangers) | |
| 1 | +1 | Matthew McDONALD (Airdrieonians) |
| +1 | Lewis VAUGHAN (Raith Rovers) | |
| +1 | Aaron COMRIE (Dunfermline) | |
| +1 | Kyle MacDONALD (Dunfermline) | |
| +1 | Callum SMITH (Hamilton) | |
| +1 | Gary MACKAY-STEVEN (Hearts) | |
| +1 | Calum BIGGAR (Queen's Park) | |
| +1 | Lewis MILNE (Montrose, 1p) | |
| +1 | Zak RUDDEN (Partick Thistle) | |
| +1 | Rabin OMAR (Stirling Albion) | |
| +1 | Ayo OBILEYE (Livingston) | |
| +1 | Lawrence SHANKLAND (Dundee United) | |
| +1 | Tom PARKES (Livingston) | |
| +1 | Martin RENNIE (Montrose) | |
| +1 | Blair LYONS (Montrose) | |
| +1 | Brian GRAHAM (Partick Thistle) | |
| +1 | Jason NAISMITH (Kilmarnock) | |
| +1 | Fraser MURRAY (Kilmarnock) | |
| +1 | Jackson LONGRIDGE (Livingston) | |
| +1 | Tony WALLACE (Annan Athletic, 1p) | |
| +1 | Luke DONNELLY (Arbroath) | |
| +1 | Liam BOYCE (Hearts) |